Abstract
In the past 10 years, the cross-coupling reactions of the relatively unreactive electrophilic aryl chlorides, -tosylates, and -mesylates have been extensively investigated. Strategies to promote oxidative addition toward inert chemical bonds have included the use of bulky, electron-rich ligands.
Access provided by Autonomous University of Puebla. Download chapter PDF
Similar content being viewed by others
Keywords
1 Introduction
The palladium-catalyzed cross-coupling reactions of organometallic reagents with aryl halides are widely used in the field of synthetic organic chemistry. These reactions are very important for creating novel functional materials and bioactive substances [1, 2]. Although numerous cross-coupling reactions have achieved the formation of carbon–carbon bonds via the cleavage of the comparatively weak bonds of aryl iodides, bromides, and triflates (C(sp2)-I, -Br, and -OTf), the synthetic success of the cross-coupling reactions cleaving the more inert bonds such as aryl chlorides, tosylates, and mesylates (C(sp2)-Cl, OTs, and OMs) has lagged behind [3, 4]. In regard to the reaction mechanism, one of the reasons why the latter substrates have not been utilized in cross-couplings is that oxidative addition of aryl chlorides, tosylates, and mesylates to the palladium center does not readily occur under standard conditions. However, around 2000 it began to be reported that the appropriate combination of certain ligands with the transition metal catalysts enables cross-coupling reactions of aryl chlorides, tosylates, and mesylates as coupling partners [5–7]. This chapter outlines the examples of the Ni and Pd-catalyzed cross-coupling reactions of the relatively inactive aryl electrophiles reported in recent years, as shown in Eq. 7.1.
2 Kumada–Tamao–Corriu Coupling
In 1984, Tamao and Kumada synthesized the coupled product 1 by using 2,6-chloropyridine and two different heteroaryl Grignard reagents as coupling partners under palladium catalysis (Scheme 7.1) [8].
Kumada-Tamao-Corriu coupling of 2,6-chloropyridine with two different heteroaryl Grignard reagents
Later, Umeno and Katayama succeeded in the first cross-coupling reactions of alkyl Grignard reagents with aryl chlorides, rather than heteroaryl chlorides. The reactions of dichloroarenes with alkyl Grignard reagents afforded the corresponding monoalkylated products 2. The double alkylated products were formed, but only in very small amounts (Eq. 7.2) [9].
In 1999, Nolan et al. reported that Kumada–Tamao–Corriu coupling reactions, catalyzed by the palladium complexes having the N-heterocyclic carbene (NHC) ligands, took place across aryl chlorides bearing electron-donating groups to afford the corresponding biaryls 3 (Eq. 7.3) [10]. However, they also reported that the reaction of a bulky 2,6-dimethylphenyl chloride with 2,4,6-trimethylphenyl Grignard reagents did not generate a corresponding product at all due to the steric hindrance.
In addition, in 2007 Organ et al. reported that a wide variety of the substrates could be applied to Kumada–Tamao–Corriu coupling reactions with various heteroaryl and aryl chlorides [11]. Recently, Kumada–Tamao–Corriu coupling reactions of aryl chlorides using nickel catalysts, rather than palladium, have been reported [12, 13]. Along that trend, Chen revealed that the nickel complexes 4, ligated by a tetradentate ligand for the Kumada–Tamao–Corriu coupling reactions, showed a high catalytic activity to generate the desired cross-coupled products 5 (Eq. 7.4) [14, 15].
Endeavors to perform Kumada–Tamao–Corriu coupling reactions with aryl tosylates have been underway in recent years. For instance, Kumada–Tamao–Corriu couplings of electron-deficient aryl tosylates with arylmagnesium reagents were demonstrated by the research group of Leitner in 2002 [16]. Later, Hartwig et al. reported coupling reactions with the aryl tosylates having various substituents in 2005 (Eq. 7.5) [17, 18]. Using palladium catalysts ligated by the bidentate ligand 6, they clarified the mechanism details of these reactions by elucidating stoichiometric reactions of the palladium complexes.
In 2006, Althammer et al. succeeded in Kumada–Tamao–Corriu coupling reactions of aryl tosylates under palladium catalysis by using the air-stable phosphonate ligands [19]. It is postulated that an equilibrium (shown in Scheme 7.2) exists for the phosphonate 7, and the active species can be stabilized through a hydrogen bond in the reaction system [20].
Kumada-Tamao-Corriu coupling of aryl tosylates using the air-stable phosphonate ligands
Knochel et al. have accomplished the cobalt(II)-catalyzed Kumada–Tamao–Corriu coupling reactions of aryl tosylates [21] and heteroaryl tosylates [22] with directing groups, achieving the in situ generation of arylcuprates from aryl bromides, Grignard reagents, and copper(I) cyanide.
3 Negishi Coupling
Negishi coupling reactions of organozinc compounds with aryl chlorides have been actively researched as well. In the 1980s, the studies started with the reactions of a variety of activated heteroaryl chlorides such as pyridines [23].
In 1994, Bracher and Hildebrand achieved the synthesis of nitramarine (8) by Negishi coupling of heteroaryl chlorides (Eq. 7.6) [24]. Negishi coupling of heteroaryl chlorides is a viable tool in various natural product syntheses to construct an array of carbon–carbon bonds (see Chap. 3).
Negishi coupling reactions of the activated aryl chlorides bearing electron-withdrawing substituents was reported by Miller and Farrell in 1998 (Eq. 7.7) [25]. They accomplished Negishi coupling reactions of aryl chlorides substituted by cyano and ester groups catalyzed by palladium and nickel as the catalysts, giving rise to the corresponding biaryls 9.
Dai and Fu explored Negishi couplings of electron-rich aryl chlorides with aryl-and alkylzinc reagents by using an electron-donating and bulky tri-tert-butylphosphine as the ligand under the palladium catalysis, giving rise to the corresponding biaryls and alkylated arenes 10 (Eq. 7.8) [26].
The analogous Negishi coupling reactions were found to take place, not only with the palladium catalysts [27–29], but also with the nickel catalysts [30]. For instance, Wang synthesized the NHC-ligated nickel complex 11 and applied this to Negishi coupling reactions with a variety of aryl chlorides [31, 32]. Recently, it was also reported that Negishi coupling of more inert aryl chlorides were smoothly accelerated under mild conditions by the palladium complex 12 bearing the NHC ligand (Fig. 7.1) [33, 34].
Active catalysts for Negishi coupling reactions of various aryl chlorides
In contrast to the large number of Negishi coupling reactions of arylzinc reagents and aryl chlorides reported, in 2009 Buchwald succeeded in Negishi coupling reactions of secondary alkylzinc compounds and a variety of aryl chlorides by using CPhos as the ligand of the palladium catalyst (Eq. 7.9) [35].
4 Migita–Kosugi–Stille Coupling
In 1998, Li et al. achieved the vinylation reactions of chloropyridine with the organotin compounds in the presence of the palladium catalyst; this was the key reaction in the synthesis of 3-AP (3-aminopyridine-2-carboxaldehyde thiosemicarbazonea) 13, the ribonucleotide reductase inhibitor (Scheme 7.3) [36].
Vinylation reactions of chloropyridine by Migita-Kosugi-Stille coupling
In 2001, Grasa and Nolan succeeded in the synthesis of the corresponding biaryls by the Migita–Kosugi–Stille coupling reactions of aryl chlorides bearing electron-poor substituents with aryltin compounds, using the palladium catalysis ligated by NHC. However, a decrease in yield was observed in the coupling reactions with aryl chlorides having the electron-donating substituents (Eq. 7.10) [37].
In 1999, Fu and Littke succeeded in the Migita–Kosugi–Stille coupling of aryl chlorides bearing electronic-rich substituents under palladium catalysis by using an electron-donating and bulky tri-tert-butylphosphine as the ligand. In addition, it was disclosed that not only aryltin compounds but also alkenyltin and alkyltin compounds could be used as the substrates (Eq. 7.11) [38, 39].
In 2004 Verkade et al. reported active catalyst systems to accelerate the coupling reactions of more inert aryl chlorides [40]. The electronic density on the phosphorus atom of the proazaphosphatrane ligands 14–17 (as shown in Eq. 7.12) is rather large because: (1) the three nitrogen atoms around the phosphorus atom share the same plane with phosphorus, and (2) the phosphorus atom has an interaction with the unpaired electron of the nitrogen atom at the bridgehead. As a result, the palladium catalysts having this ligand generally show high catalytic activity toward inert aryl chlorides.
Although the use of palladium as a catalyst is frequent in the cross-coupling reactions of aryl chlorides [41–43], in 2006 Zhang reported that copper(I) oxide can catalyze the coupling reactions of aryl chlorides and aryltin compounds through the assistance of appropriate activators (Eq. 7.13) [44].
5 Suzuki–Miyaura Coupling
In the 1980s, Suzuki–Miyaura coupling reactions of aryl chlorides with organoboron compounds were reported for the first time by Terashima (Eq. 7.14) [45]. In this reaction, the desired bipyridine was obtained from 2-chloropyridine as a coupling partner by using Pd(PPh3)4 as the catalyst.
Through the use of palladium with triarylphosphine ligands, the cross-coupling reactions of a variety of heteroaromatic chlorides were achieved. In the 1990s, it began to be reported that the cross-coupling reactions of arylboronic acids with aryl chlorides afforded the target biaryls utilizing a substrate bearing electron-withdrawing groups, such as nitro, cyano, and acetyl groups, in the presence of the palladium catalysts ligated with arylphosphines [46]. Moreover, reactions using the catalysts with high turnover numbers (TONs) were reported (Eq. 7.15) [47]
Pioneering research in this field was reported in 1998. Fu accomplished the cross-coupling of electron-rich aryl chlorides utilizing a bulky alkylated phosphine ligand (Eq. 7.16, condition A) [48]. Meanwhile, Buchwald succeeded in obtaining the cross-coupled products in high yields from unactivated aryl chlorides by using the phosphine ligand 18, consisting of a biaryl backbone (Eq. 7.16, condition B) [49–52].
Since the initial discovery, a large number of researchers have created a myriad of these catalysts for effective Suzuki–Miyaura coupling reactions of aryl chlorides (Fig. 7.2). In recent years, copious examples of the Suzuki–Miyaura coupling reactions accomplished with highly electron-donating, bulky phosphorus-containing ligands [53–60], the biaryl-type phosphine ligands [61–63], and the NHC (N-hetrocyclic carbene) ligands [64–67] of the palladium catalysts have been reported [53, 54, 63, 68].
Various palladium catalysts effective for Suzuki–Miyaura couplings of aryl chlorides
Enhancements such as milder reaction conditions have also been attained; for instance, the room-temperature reactions of highly active catalysts have been developed. In 2004, the NHC ligands with a powerful ability to accelerate Suzuki–Miyaura coupling reactions toward the bulky and electron-rich substrates were synthesized (Eq. 7.17) [69]. In these reactions, even if both the aryl chlorides and the arylboronic acids were sterically congested, the corresponding biaryl compounds were obtained in high yields.
In 2005, Buchwald similarly reported that the Suzuki–Miyaura couplings occured for the bulky substrates in water by introducing sodium sulphonate into the aryl group of the biaryl-type ligands [70]. It was reported that other ligands involving polymers such as the silica gel, tetraethylene glycol, and polystyrenes also showed a high performance [58, 71–74]. In the reactions reported by Tsuji, the TEG-containing ligand 19 captures the metal catalysts, generating coordinatively unsaturated catalyst species (Fig. 7.3). The formed active catalysts accelerate oxidative addition of the carbon-chlorine bond, leading to the smooth cross-coupling reactions of the electron-rich aryl chlorides [75–78].
Active ligand containing the TEG moieties
In addition to the aforementioned active catalysts, recently recyclable heterogeneous catalysts were synthesized for use in Suzuki–Miyaura couplings [79]. This new type of catalyst consists of nano particles of iron oxide (Fe3O4) on silica gel; the film-supported catalysts have been used for the Suzuki–Miyaura couplings. The catalysts were found to be easily separable from the reaction mixtures with a magnet after completion of the reactions, and they can be recycled many times. Moreover, the catalysts can be applicable to Sonogashira–Hagiwara as well as Migita–Kosugi–Stille couplings under slightly modified reaction conditions.
Although arylboronic acids have been widely utilized as coupling partners in the Suzuki–Miyaura coupling reactions of aryl chlorides, in 2004 Buchwald reported coupling reactions utilizing potassium aryltrifluoroborates [80]. Furthermore, Molander reported Suzuki–Miyaura coupling reactions of aryl chlorides with alkoxymethyltrifluoroborates (Eq. 7.18) [81] and with cyclopropyl- and cyclobutyltrifluoroborates (Scheme7.4) [82].
Suzuki-Miyaura coupling of aryl chlorides with cyclopropyl- and cyclobutyltrifluoroborates
Colobert reported the NHC-ligated-palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with lithium alkynylborates as coupling partners to give the corresponding internal ethynes (Eq. 7.19) [83].
In 2010, Dreher synthesized the corresponding biaryls 20 from the subsequent Suzuki–Miyaura cross-coupling reactions of tetrahydroxydiborane with two different aryl chlorides in one pot (Scheme 7.5) [84].
Suzuki-Miyaura coupling of tetrahydroxydiborane with two different aryl chlorides
In this reaction, it is thought that solubility and reactivity are enhanced by using ethanol as the solvent. The equilibrium between tetrahydroxydiborane (21) and ethanol creates a variety of ethyl ethers to generate dipinacolboron-like species, as shown in Scheme 7.6.
The equilibrium between tetrahydroxydiborane (21) and tetraethoxydiborane
On the other hand, Suzuki–Miyaura coupling reactions of aryl mesylates bearing electron-withdrawing groups, catalyzed by nickel, were reported for the first time by the research group of Hill in 1995 [85]. Moreover, in 1996 Kobayashi et al. similarly reported the Suzuki–Miyaura coupling reactions of aryl tosylates and mesylates with phenylboronic acid in the presence of the nickel catalysts (Eq. 7.20) [86]. Unfortunately, the substrate scope was found to be very narrow, and the reaction only took place with aryl tosylates and mesylates that have electron-withdrawing substituents.
After 2000, Suzuki–Miyaura coupling reactions of aryl tosylates with arylboronic acids bearing various substituents were reported by Monteiro using the alkylphosphine ligands under nickel catalysis [87]. In 2002 Boggess reported the coupling reactions of heteroaryl tosylates with arylboronic acids by using the sterically bulky phosphine ligand, XPhos (see, Scheme 7.4), in the presence of the palladium catalysts [88]. In 2004 Buchwald et al. reported Suzuki–Miyaura coupling reactions of various aryl tosylates, which greatly contributed to the expansion of the substrate scope (Eq. 7.21) [89].
With these nickel catalysts in hand, coupling reactions of a series of aryl mesylates were reported [90]. The analogous coupling reactions with aryl tosylates were attained at room temperature by Hu et al. (Eq. 7.22) [91]. As the result of the precedent works, a large number of reactions were reported using similar ligands [92–95]. Later, improvements of amounts and ease of handling of the catalysts were achieved to realize more coupling reactions [96–99].
Furthermore, it has been reported that the preparation of the corresponding arylboronic acids from aryl halides, followed by the coupling reactions with aryl tosylates or mesylates can obtain the target biaryl compounds 22 (Scheme 7.7) [100].
Suzuki-Miyaura coupling with aryl tosylates or mesylates
6 Hiyama Coupling
In 1975 Matsumoto et al. were the first to succeed in the trimethylsilylation of aryl chlorides bearing a nitro group with hexamethyldisilane (Eq. 7.23) [101]. They also proved that the carbon–carbon bonds are easily formed by cleavage of the carbon-chlorine bond in the 2-position, analogous to the reactions with 2,5-dichloronitorobenzene as the coupling partner [102].
Since the latter half of the 1990s, many researchers have reported coupling reactions for a variety of aryl compounds bearing the silicon functional groups [103–106]. Hatanaka and Hiyama expanded the substrate scope in 1996, reporting the coupling reactions of aryl chlorides bearing various electron-withdrawing groups with arylsilicon compounds (Eq. 7.24) [107].
In addition, Hiyama et al. also reported coupling reactions with alkenylsilicon compounds (Eq. 7.25). The reactivity of alkenylchlorosilanes was found to be strongly influenced by the structure of the silyl groups; the cross-coupling reaction of (E)-1-octenylchlorosilanes bearing a SiCl3 group was the fastest. It should be noted that these coupling reactions proceeded with the retention of the double bond geometry of the alkenylchlorosilanes.
Very recently, Verkade et al. synthesized the new phosphine ligand 23, with a high electron-donating ability, which was found to smoothly undergo the reactions of various substituted aryl chlorides (Eq. 7.26) [108]. With this catalyst system in hand, the corresponding biaryls were obtained with the electron-rich aryl chlorides.
One of many examples of Hiyama coupling, the reaction of aryl tosylates, has been reported by Wu in 2008 (Eq. 7.27) [109]. Subsequently, the extended coupling reactions with aryl mesylates were reported by the same research group [110]. In 2009 Kwong et al. succeeded in more efficient reactions by using the indole-type ligands under the palladium catalysis [111].
Only one example of a nickel version of coupling reactions of aryl tosylates was reported; Hiyama et al. very recently accomplished this by using the mixed system of two different phosphine ligands (Eq. 7.28) [112]. Importantly, an aryl mesylate also participated in the coupling reaction to give the biaryl.
7 Sonogashira–Hagihara Coupling
The Sonogashira–Hagihara coupling reactions of aryl chlorides with terminal alkynes were ardently researched by many chemists in the latter half of the 1980s. More recently, the Sonogashira–Hagihara coupling reactions of aryl chlorides bearing the electron-withdrawing groups have gradually been investigated (Scheme 7.8) [113, 114]. The coupling reaction of 4-chloro-3-cyanopyridine with phenylethyne gave 4-(phenylethynyl)pyridine, which smoothly underwent the intramolecular cyclization under acidic conditions to afford 3-pheynl-1H-pyrano[3,4-c]pyridin-1-one (24).
Sonogashira-Hagihara coupling with aryl chlorides
Meanwhile, Lanza et al. synthesized the corresponding arylethynes from aryl chlorides having a nitro group in the 2-position. They further demonstrated the synthesis of an indole 25 bearing a substituent in the 6-position by four steps (Scheme 7.9) [115].
Synthesis of arylethynes from aryl chlorides having a nitro group in the 2-position
Sonogashira–Hagihara coupling reactions with aryl chlorides that bear various substituents have been manifestly reported since 2000. For instance, in 2003 Plenio reported Sonogashira–Hagihara coupling of the unactivated aryl chlorides without copper (I) salts as a co-catalyst (Eq. 7.29) [116].
In the same year, Buchwald reported that Sonogashira–Hagihara coupling reactions of a variety of aryl chlorides smoothly proceeded in the presence of the palladium catalysts ligated by XPhos (see Scheme 7.4) (Eq. 7.30) [117]. This reaction overcame the prior limitations of substrates. In the past, coupling reactions of aryl chlorides bearing electron-rich substituents at the ortho position had not taken place easily.
In 2007, Hua et al. reported the reactions of aryl chlorides affording the symmetrical diarylethynes in one pot (Eq. 7.31) [118]. In this reaction, the same aryl groups can be introduced to both ends of the ethyne by using 1,1-dimethylpropargylalcohol as a substrate. Although most of the reactions reported thus far have employed the palladium catalysts [119–125], Prajapati reported the Sonogashira–Hagihara reactions catalyzed by indium(III) in 2005 [126].
In 2008 the unsymmetrical diarylethynes were synthesized directly by activating the silicon–carbon bond of trimethylsilylethyne derivatives with copper(I) chloride, rather than using the terminal alkynes as the substrates in the classical Sonogashira–Hagihara couplings (Eq. 7.32) [127].
In 2003, for the first time, Sonogashira–Hagihara coupling reactions with aryl tosylates were reported by Buchwald (Eq. 7.33) [128]. In these reactions, slow addition of the alkynes is essential to form the desired products in high yields.
Recently Kwong has reported Sonogashira–Hagihara coupling reactions with aryl mesylates by using the indole-containing phosphine ligand 26 (Fig. 7.4, left) under palladium catalysis [129]. Furthermore, the coupling reactions of aryl mesylates and -tosylates have been attained more efficiently by using ligand 27 (Fig. 7.4, right) [130].
Effective ligands 26 and 27 for palladium-catalyzed Sonogashira coupling reactions with aryl tosylates, -mesylates, and -tosylates
8 Summary
In this chapter, examples of the cross-coupling reactions with aryl chlorides, -mesylates, and -tosylates reported in recent years have been introduced. One can expect to utilize these reactions further for innovative syntheses of natural products and of functional materials with new physical properties. Moreover, in the future, not only the carbon–chlorine bond but also more inert bonds will likely be selectively activated. As a result, the development of new types of cross-coupling reactions that can precisely introduce the desired substituents at the desired position may be achieved.
References
Diederich F, Stang PJ (1998) Metal-catalyzed cross-coupling reactions. Wiley, New York
Tsuji J (1995) Palladium reagents and catalysts, innovations in organic synthesis. Wiley, New York
Brandsma L, Vasilevsky SF, Verkruijsse HD (1998) Application of transition metal catalysts in organic synthesis, vol 150. Springer, New York, pp 228–229
Geissler H (1998) Transition metals for organic synthesis, vol 1. In: Beller M, Bolm C (eds). Wiley, New York
Grushin VV, Alper H (1999) Activation of unreactive bonds and organic synthesis. In: Murai S (ed) Topics in organometallic chemistry. Springer, Berlin
Herrmann WA (2002) Applied homogeneous catalysis with organometallic compounds, vol 1 In: Cornils B, Herrmann WA (eds) A comprehensive handbook. Wiley, Weinheim
Fu GC, Littke AF (2002) Palladium-catalyzed coupling reactions of aryl chlorides. Angew Chem Int Ed 41:4176–4211
Minato A, Suzuki K, Tamao K, Kumada M (1984) Mixed heteroarene oligomers. J Chem Soc Chem Commun, 511–513
Katayama T, Umeno M (1991) Selective mono-alkylation and arylation of dichlorobenzenes by palladium-catalyzed Grignard cross-coupling. Chem Lett, 2073–2076
Huang J, Nolan SP (1999) Efficient cross-coupling of aryl chlorides with aryl Grignard reagents (Kumada reaction) mediated by a palladium/imidazolium chloride system. J Am Chem Soc 121:9889–9890
Organ MG, Abdel-Hadi M, Avola S, Hadei N, Nasielski J, O’Brien CJ, Valente C (2007) Biaryls made easy: PEPPSI and the Kumada–Tamao–Corriu reaction. Chem Eur J 13:150–157
Zhang C, Wang Z (2009) N-heterocyclic carbene-based nickel complexes: synthesis and catalysis in cross-couplings of aryl chlorides with ArMX (M = Mg or Zn). Organometallics 28:6507–6514
Ghosh R, Sarkar A (2010) Bidentate P, N–P ligand for nickel-catalyzed cross-coupling of aryl or benzyl chlorides with ArMgX. J Org Chem 75:8283–8286
Xi Z, Liu B, Chen W (2008) Room-temperature Kumada cross-coupling of unactivated aryl chlorides catalyzed by N-heterocyclic carbene-based nickel(II) complexes. J Org Chem 73:3954–3957
Liu A, Zhang X, Chen W (2009) New pincer CC’C complexes of nickel(II) via chloronickelation of alkyne-bearing N-heterocyclic carbenes. Organometallics 28:4868–4871
Fürstner A, Leitner A (2002) Iron-catalyzed cross-coupling reactions of alkyl-Grignard reagents with aryl chlorides, tosylates, and triflates. Angew Chem Int Ed 41:609–612
Roy AH, Hartwig JF (2003) Oxidative addition of aryl tosylates to palladium(0) and coupling of unactivated aryl tosylates at room temperature. J Am Chem Soc 125:8704–8705
Limmert ME, Roy AH, Hartwig JF (2005) Kumada coupling of aryl and vinyl tosylates under mild conditions. J Org Chem 70:9364–9370
Ackermann L, Althammer A (2006) Air-stable PinP(O)H as preligand for palladium-catalyzed Kumada couplings of unactivated tosylates. Org Lett 8:3457–3460
Ackermann L, Kapdi AR, Fenner S, Kornhaaß C, Schulzke C (2011) Well-defined air-stable palladium HASPO complexes for efficient Kumada–Corriu cross-couplings of (hetero)aryl or alkenyl tosylates. Chem Eur J 17:2965–2971
Korn TJ, Schade MA, Wirth S, Knochel P (2006) Cobalt(II)-catalyzed cross-coupling between polyfunctional arylcopper reagents and aryl fluorides or tosylates. Org Lett 8:725–728
Korn TJ, Schade MA, Cheemala MN, Wirth S, Guevara SA, Cahiez G, Knochel P (2006) Cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with arylmagnesium halides and of polyfunctionalized arylcopper reagents with aryl bromides, chlorides, fluorides and tosylates. Synthesis, 3547–3574
Amat M, Hadida S, Pshenichnyi G, Bosch J (1997) Palladium(0)-catalyzed heteroarylation of 2- and 3-indolylzinc derivatives. An efficient general method for the preparation of (2-pyridyl)indoles and their application to indole alkaloid synthesis. J Org Chem 62:3158–3175
Bracher F, Hildebrand D (1994) 1,9-dimetalated ß-carbolines. Versatile building blocks for the total synthesis of alkaloids. Tetrahedron 50:12329–12336
Miller JA, Farrell RP (1998) Synthesis of functionally substituted unsymmetrical biaryls via a novel double metal catalyzed coupling reaction. Tetrahedron Lett 39:7275–7278
Dai C, Fu GC (2001) The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd(P(t-Bu)3)2 as a catalyst. J Am Chem Soc 123:2719–2724
Palladium catalyzed coupling reaction: Li GY (2002) Highly active, air-stable palladium catalysts for the C–C and C–S bond-forming reactions of vinyl and aryl chlorides: use of commercially available [(t-Bu)2P(OH)]2PdCl2, [(t-Bu)2P(OH)PdCl2]2, and [[(t-Bu)2PO···H···OP(t-Bu)2]PdCl]2 as catalysts. J Org Chem 67:3643–3650
Walla P, Kappe CO (2004) Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides. Chem Commun, 564–565
Luzung MR, Patel JS, Yin J (2010) A mild Negishi cross-coupling of 2-heterocyclic organozinc reagents and aryl chlorides. J Org Chem 75:8330–8332
Wang L, Wang Z (2007) Efficient cross-coupling of aryl chlorides with arylzinc reagents catalyzed by amido pincer complexes of nickel. Org Lett 9:4335–4338
Xi Z, Zhou Y, Chen W (2008) Efficient Negishi coupling reactions of aryl chlorides catalyzed by binuclear and mononuclear nickel-N-heterocyclic carbene complexes. J Org Chem 73:8497–8501
Liu N, Wang L, Wang Z (2011) Room-temperature nickel-catalysed cross-couplings of aryl chlorides with arylzincs. Chem Commun, 1598–1600
Zhang C, Wang Z (2009) N-heterocyclic carbene-based nickel complexes: synthesis and catalysis in cross-couplings of aryl chlorides with ArMX (M = Mg or Zn). Organometallics 28:6507–6514
Çalimsiz S, Sayah M, Mallik D, Organ MG (2010) Pd-PEPPSI-IPent: low-temperature Negishi cross-coupling for the preparation of highly functionalized, tetra-ortho-substituted biaryls. Angew Chem Int Ed 49:2014–2017
Han C, Buchwald SL (2009) Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides. J Am Chem Soc 131:7532–7533
Li J, Chen S, Li X, Niu C, Doyle TW (1998) Efficient synthesis of ribonucleotide reductase inhibitors 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) and 3-amino-4-methylpyridine-2-carboxaldehyde thiosemicarbazone (3-AMP) via palladium mediated cross-coupling reactions. Tetrahedron 54:393–400
Grasa GA, Nolan SP (2001) Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates. Org Lett 3:119–122
Littke AF, Fu GC (1999) The first general method for Stille cross-couplings of aryl chlorides. Angew Chem Int Ed 38:2411–2413
Littke AF, Schwarz L, Fu GC (2002) Pd/P(t-Bu)3: a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides. J Am Chem Soc 124:6343–6348
Su W, Urgaonkar S, McLaughlin PA, Verkade JG (2004) Highly active palladium catalysts supported by bulky proazaphosphatrane ligands for Stille cross-coupling: coupling of aryl and vinyl chlorides, room temperature coupling of aryl bromides, coupling of aryl triflates, and synthesis of sterically hindered biaryls. J Am Chem Soc 126:16433–16439
Mee SPH, Lee V, Baldwin JE (2005) Significant enhancement of the Stille reaction with a new combination of reagents—copper(I) iodide with cesium fluoride. Chem Eur J 11:3294–3308
Coelho AV, Souza ALF, Lima PG, Wardell JL, Antunes OAC (2008) Stille cross-coupling reaction using Pd/BaSO4 as catalyst reservoir Appl Organomet Chem 22:39–42
Naber JR, Buchwald SL (2008) Palladium-catalyzed Stille cross-coupling reaction of aryl chlorides using a pre-milled palladium acetate and XPhos catalyst system. Adv Synth Catal 350:957–961
Li J, Tang B, Tao L, Xie Y, Liang Y, Zhang M (2006) Reusable copper-catalyzed cross-coupling reactions of aryl halides with organotins in inexpensive ionic liquids. J Org Chem 71:7488–7490
Ishikura M, Kamada M, Terashima M (1984) An efficient synthesis of 3-heteroarylpyridines via diethyl-(3-pyridyl)-borane. Synthesis, 936–938
Shen W (1997) Palladium catalyzed coupling of aryl chlorides with arylboronic acids. Tetrahedron Lett 38:5575–5578
Feuerstein M, Doucet H, Santelli M (2001) Palladium catalysed cross-coupling of aryl chlorides with arylboronic acids in the presence of a new tetraphosphine ligand. Synlett, 1458–1460
Littke AF, Fu GC (1998) A convenient and general method for Pd-catalyzed Suzuki cross-couplings of aryl chlorides and arylboronic acids. Angew Chem Int Ed 37:3387–3388
Wolfe JP, Buchwald SL (1999) A highly active catalyst for the room-temperature amination and Suzuki coupling of aryl chlorides. Angew Chem Int Ed 38:2413–2416
Wolfe JP, Singer RA, Yang BH, Buchwald SL (1999) Highly active palladium catalysts for Suzuki coupling reactions. J Am Chem Soc 121:9550–9561
Yin J, Buchwald SL (2000) A catalytic asymmetric Suzuki coupling for the synthesis of axially chiral biaryl compounds. J Am Chem Soc 122:12051–12052
Lakshman MK, Hilmer JH, Martin JQ, Keeler JC, Dinh YQV, Ngassa FN, Russon LM (2001) Palladium catalysis for the synthesis of hydrophobic C-6 and C-2 aryl 2′-deoxynucleosides. Comparison of C–C versus C–N bond formation as well as C-6 versus C-2 reactivity. J Am Chem Soc 123:7779–7787
Fleckenstein CA, Plenio H (2008) Efficient Suzuki–Miyaura coupling of (hetero)aryl chlorides with thiophene- and furanboronic acids in aqueous n-butanol. J Org Chem 73:3236–3244
Hoshi T, Nakazawa T, Saitoh I, Mori A, Suzuki T, Sakai J, Hagiwara H (2008) Biphenylene-substituted ruthenocenylphosphine for Suzuki–Miyaura coupling of aryl chlorides. Org Lett 10:2063–2066
Jackson J, Xia A (2009) Novel bulky pyrazolylphosphine ligands for the Suzuki coupling of aryl chlorides. Tetrahedron Lett 50:7217–7219
So CM, Yeung CC, Lau CP, Kwong FY (2008) A new family of tunable indolylphosphine ligands by one-pot assembly and their applications in Suzuki–Miyaura coupling of aryl chlorides. J Org Chem 73:7803–7806
Blug M, Guibert C, Goff X-FL, Mézailles N, Floch PL (2009) 1-Phosphabarrelene complexes of palladium and their use in Suzuki–Miyaura coupling reactions. Chem Commun, 201–203
Yang DX, Colletti SL, Wu K, Song M, Li GY, Shen HC (2009) Palladium-catalyzed Suzuki–Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands. Org Lett 11:381–384
Lü B, Fu C, Ma S (2010) Application of a readily available and air stable monophosphine HBF4 salt for the Suzuki coupling reaction of aryl or 1-alkenyl chlorides. Tetrahedron Lett 51:1284–1286
Bobadilla MVE, Teuma E, Bultob AMM, Gomez M (2011) New bicyclic phosphorous ligands: synthesis, structure and catalytic applications in ionic liquids. Tetrahedron 67:421–428
So CM, Lau CP, Kwong FY (2007) Easily accessible and highly tunable indolyl phosphine ligands for Suzuki–Miyaura coupling of aryl chlorides. Org Lett 9:2795–2798
So CM, Chow WK, Choy PY, Lau CP, Kwong FY (2010) Remarkably effective phosphanes simply with a PPh2 moiety: application to Pd-catalysed cross-coupling reactions for tetra-ortho-substituted biaryl syntheses. Chem Eur J 16:7996–8001
Molander GA, Shin I, Jean-Gérard L (2010) Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides. Org Lett 12:4384–4387
Brendgen T, Frank M, Schatz J (2006) The Suzuki coupling of aryl chlorides in aqueous media catalyzed by in situ generated calix[4]arene-based N-heterocyclic carbene ligands. Eur J Org Chem, 2378–2383
Fleckenstein C, Roy S, Leuthäußer S, Plenio H (2007) Sulfonated N-heterocyclic carbenes for Suzuki coupling in water. Chem Commun, 2870–2872
Diebolt O, Braunstein P, Nolan SP, Cazin CSJ (2008) Room-temperature activation of aryl chlorides in Suzuki–Miyaura coupling using a [Pd(μ-Cl)Cl(NHC)]2 complex (NHC = N-heterocyclic carbene). Chem Commun, 3190–3192
Karimi B, Akhavan PF (2009) Main-chain NHC-palladium polymer as a recyclable self-supported catalyst in the Suzuki–Miyaura coupling of aryl chlorides in water. Chem Commun, 3750–3752
Jackson J, Xia A (2009) Novel bulky pyrazolylphosphine ligands for the Suzuki coupling of aryl chlorides. Tetrahedron Lett 50:7217–7219
Altenhoff G, Goddard R, Lehmann CW, Glorius F (2004) Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis. J Am Chem Soc 126:15195–15201
Anderson KW, Buchwald SL (2005) General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water. Angew Chem Int Ed 44:6173–6177
Sayah R, Glegoła K, Framery E, Dufaud V (2007) Suzuki–Miyaura reactions of aryl chloride derivatives with arylboronic acids using mesoporous silica-supported aryldicyclohexylphosphine. Adv Synth Catal 349:373–381
Schweizer S, Becht JM, Drian CL (2007) Highly efficient and reusable supported Pd catalysts for Suzuki–Miyaura reactions of aryl chlorides. Org Lett 9:3777–3780
Fujihara T, Yoshida S, Terao J, Tsuji Y (2009) A triarylphosphine ligand bearing dodeca(ethylene glycol) chains: enhanced efficiency in the palladium-catalyzed Suzuki–Miyaura coupling reaction. Org Lett 11:2121–2124
Schweizer S, Becht JM, Drian CL (2010) Highly efficient reusable polymer-supported Pd catalysts of general use for the Suzuki reaction. Tetrahedron 66:765–772
Niyomura O, Tokunaga M, Obora Y, Iwasawa T, Tsuji Y (2003) Rate enhancement with a bowl-shaped phosphane in the rhodium-catalyzed hydrosilylation of ketones. Angew Chem Int Ed 42:1287–1289
Niyomura O, Iwasawa T, Sawada N, Tokunaga M, Obora Y, Tsuji Y (2005) A bowl-shaped phosphine as a ligand in rhodium-catalyzed hydrosilylation: rate enhancement by a mono(phosphine) rhodium species. Organometallics 24:3468–3475
Iwasawa T, Komano T, Tajima A, Tokunaga M, Obora Y, Fujihara T, Tsuji Y (2006) Phosphines having a 2,3,4,5-tetraphenylphenyl moiety: effective ligands in palladium-catalyzed transformations of aryl chlorides. Organometallics 25:4665–4669
Ohta H, Tokunaga M, Obora Y, Iwai T, Iwasawa T, Fujihara T, Tsuji Y (2007) A bowl-shaped phosphine as a ligand in palladium-catalyzed Suzuki–Miyaura coupling of aryl chlorides: effect of the depth of the bowl. Org Lett 9:89–92
Jin MJ, Lee DH (2010) A practical heterogeneous catalyst for the Suzuki, Sonogashira, and Stille coupling reactions of unreactive aryl chlorides. Angew Chem Int Ed 49:1119–1122
Barder TE, Buchwald SL (2004) Efficient catalyst for the Suzuki–Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides. Org Lett 6:2649–2652
Molander GA, Canturk B (2008) Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides. Org Lett 10:2135–2138
Molander GA, Gormisky PE (2008) Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides. J Org Chem 73:7481–7485
Torres GH, Choppin S, Colobert F (2006) Efficient Suzuki–Miyaura coupling reactions between lithium alkynyltrimethylborates and aryl chlorides. Eur J Org Chem, 1450–1454
Molander GA, Trice SLJ, Dreher SD (2010) Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives. J Am Chem Soc 132:17701–17703
Percec V, Bae J-Y, Hill DH (1995) Aryl mesylates in metal catalyzed homocoupling and cross-coupling reactions. 2. Suzuki-type nickel-catalyzed cross-coupling of aryl arenesulfonates and aryl mesylates with arylboronic acids. J Org Chem 60:1060–1065
Kobayashi Y, Mizojiri R (1996) Nickel-catalyzed coupling reaction of lithium organoborates and aryl mesylates possessing an electron withdrawing group. Tetrahedron Lett 37:8531–8534
Zim D, Lando VR, Dupont J, Monteiro AL (2001) NiCl2(PCy3)2: a simple and efficient catalyst precursor for the Suzuki cross-coupling of aryl tosylates and arylboronic acids. Org Lett 3:3049–3051
Lakshman MK Thomson PF, Nuqui MA, Hilmer JH, Sevova N, Boggess B (2002) Facile Pd-catalyzed cross-coupling of 2\(^\prime\)-deoxyguanosine O 6-arylsulfonates with arylboronic acids, Org Lett 4:1479–1482
Nguyen HN, Huang X, Buchwald SL (2003) The first general palladium catalyst for the Suzuki–Miyaura and carbonyl enolate coupling of aryl arenesulfonates. J Am Chem Soc 125:11818–11819
Percec V, Golding GM, Smidrkal J, Weichold O (2004) NiCl2(dppe)-catalyzed cross-coupling of aryl mesylates, arenesulfonates, and halides with arylboronic acids. J Org Chem 69:3447–3452
Tang Z, Hu Q (2004) Room-temperature Ni(0)-catalyzed cross-coupling reactions of aryl arenesulfonates with arylboronic acids. J Am Chem Soc 126:3058–3059
Zhang L, Meng T, Wu J (2007) Palladium-catalyzed Suzuki–Miyaura cross-couplings of aryl tosylates with potassium aryltrifluoroborates. J Org Chem 72:9346–9349
So CM, Lau CP, Chan ASC, Kwong FY (2008) Suzuki–Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine–palladium catalysts. J Org Chem 73:7731–7734
Bhayana B, Fors BP, Buchwald SL (2009) A versatile catalyst system for Suzuki–Miyaura cross-coupling reactions of C(sp2)-tosylates and mesylates. Org Lett 11:3954–3957
Chow WK, So CM, Lau CP, Kwong FY (2011) Palladium-catalyzed borylation of aryl mesylates and tosylates and their applications in one-pot sequential Suzuki–Miyaura biaryl synthesis. Chem Eur J 17:6913–6917
Kuroda J, Inamoto K, Hiroya K, Doi T (2009) N-heterocyclic carbene derived nickel–pincer complexes: efficient and applicable catalysts for Suzuki–Miyaura coupling reactions of aryl/alkenyl tosylates and mesylates. Eur J Org Chem, 2251–2261
Tu T, Mao H, Herbert C, Xu M, Dötz KH (2010) A pyridine-bridged bis-benzimidazolylidene pincer nickel(II) complex: synthesis and practical catalytic application towards Suzuki–Miyaura coupling with less-activated electrophiles. Chem Commun, 7796–7798
Gao H, Li Y, Zhou Y, Han FS, Lin Y (2011) Highly efficient Suzuki–Miyaura coupling of aryl tosylates and mesylates catalyzed by stable, cost-effective [1,3-bis(diphenylphosphino)propane]nickel(II) chloride [Ni(dppp)Cl2] with only 1 mol% loading. Adv Synth Catal 353:309–314
Xing C, Lee J, Tang Z, Zheng J, Hu Q (2011) Room temperature nickel(II) complexes [(4-MeOC6H4)Ni(PCy3)2OTs and Ni(PCy3)2X2]-catalyzed cross-coupling reactions of aryl/alkenyl sulfonates with arylboronic acids. Adv Synth Catal 353:2051–2059
Wilson DA, Wilson CJ, Rosen BM, Percec V (2008) Two-step, one-pot Ni-catalyzed neopentylglycolborylation and complementary Pd/Ni-catalyzed cross-coupling with aryl halides, mesylates, and tosylates. Org Lett 10:4879–4882
Matsumoto H, Nagashima S, Yoshihiro K, Nagai Y (1975) Silicon–carbon bond formation by the reaction of disilanes with halobenzenes in the presence of tetrakis(triphenylphosphine)palladium(0). J Organomet Chem 85:C1–C3
Matsumoto H, Shono K, Nagai Y (1981) The reaction of hexamethyldisilane with dihalonitrobenzenes in the presence of tetrakis(triphenylphosphine)palladium(0). Synthesis of bis(trimethylsilyl)nitrobenzenes and (trimethylsilyl)chloronitrobenzenes. J Organomet Chem 208:145–152
Hagiwara E, Gouda K, Hatanaka Y, Hiyama T (1997) NaOH-promoted cross-coupling reactions of organosilicon compounds with organic halides: practical routes to biaryls, alkenylarenes and conjugated dienes. Tetrahedron Lett 38:439–442
Mowery ME, DeShong P (1999) Improvements in cross coupling reactions of hypervalent siloxane derivatives. Org Lett 1:2137–2140
Lee HM, Nolan SP (2000) Efficient cross-coupling reactions of aryl chlorides and bromides with phenyl- or vinyltrimethoxysilane mediated by a palladium/imidazolium chloride system. Org Lett 2:2053–2055
Ju J, Nam H, Jung HM, Lee S (2006) Palladium-catalyzed cross-coupling of trimethoxysilylbenzene with aryl bromides and chlorides using phosphite ligands. Tetrahedron Lett 47:8673–8678
Gouda K, Hagiwara E, Hatanaka Y, Hiyama T (1996) Cross-coupling reactions of aryl chlorides with organochlorosilanes: highly effective methods for arylation or alkenylation of aryl chlorides. J Org Chem 61:7232–7233
Raders SM, Kingston JV, Verkade JG (2010) Advantageous use of tBu2P-N=P(iBuNCH2CH2)3N in the Hiyama coupling of aryl bromides and chlorides. J Org Chem 75:1744–1747
Zhang L, Wu J (2008) Palladium-catalyzed Hiyama cross-couplings of aryl arenesulfonates with arylsilanes. J Am Chem Soc 130:12250–12251
Zhang L, Qing J, Yang P, Wu J (2008) Palladium-catalyzed Hiyama cross-coupling reactions of aryl mesylates. Org Lett 10:4971–4974
So CM, Lee HW, Lau CP, Kwong FY (2009) Palladium–indolylphosphine-catalyzed Hiyama cross-coupling of aryl mesylates. Org Lett 11:317–320
Tang S, Takeda M, Nakao Y, Hiyama T (2011) Nickel-catalysed cross-coupling reaction aryl(trialkyl)silanes with aryl chlorides and tosylates. Chem Commun, 307–309
Sakamoto T, An-naka M, Kondo Y, Araki T, Yamanaka H (1988) Condensed heteroaromatic ring systems. XV.: synthesis of pyranopyridinones from halopyridinecarbonitriles. Chem Pharm Bull 36:1890–1894
Sakamoto T, Kondo Y, Yamanaka H (1986) Condensed heteroaromatic ring systems. VI.: synthesis of indoles and pyrrolopyridines from o-nitroarylacetylenes. Chem Pharm Bull 34:2362–2368
Tischler AN, Lanza TJ (1986) 6-Substituted indoles from o-halonitrobenzenes. Tetrahedron Lett 27:1653–1656
Köllhofer AK, Pullmann T, Plenio H (2003) A versatile catalyst for the Sonogashira coupling of aryl chlorides. Angew Chem Int Ed 42:1056-1058
Gelman D, Buchwald SL (2003) Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: use of a copper cocatalyst inhibits the reaction. Angew Chem Int Ed 42:5993–5996
Yi C, Hua R, Zeng H, Huang Q (2007) Palladium-catalyzed efficient and one-pot synthesis of diarylacetylenes from the reaction of aryl chlorides with 2-methyl-3-butyn-2-ol. Adv Synth Catal 349:1738–1742
Hierso JC, Fihri A, Amardeil R, Meunier P (2004) Catalytic efficiency of a new tridentate ferrocenyl phosphine auxiliary: Sonogashira cross-coupling reactions of alkynes with aryl bromides and chlorides at low catalyst loadings of 10–1 to 10–4 mol%. Org Lett 6:3473–3476
Liang Y, Xie Y, Li J (2006) Modified palladium-catalyzed Sonogashira cross-coupling reactions under copper-, amine-, and solvent-free conditions. J Org Chem 71:379–381
Yi C, Hua R (2006) Efficient copper-free PdCl2(PCy3)2-catalyzed Sonogashira coupling of aryl chlorides with terminal alkynes. J Org Chem 71:2535–2537
Huang H, Liu H, Jiang H, Chen K (2008) Rapid and efficient Pd-catalyzed Sonogashira coupling of aryl chlorides. J Org Chem 73:6037–6040
Komáromi A, Novák Z (2008) Efficient copper-free Sonogashira coupling of aryl chlorides with palladium on charcoal. Chem Commun, 4968–4970
Lee DH, Lee YH, Harrowfield JM, Lee IM, Lee HI, Lim WT, Kim Y, Jin MJ (2009) Phosphine-free Sonogashira coupling: reactions of aryl halides catalysed by palladium(II) complexes of azetidine-derived polyamines under mild conditions. Tetrahedron 65:1630–1634
Mphahlele MJ (2010) Regioselective alkynylation of 2-aryl-4-chloro-3-iodoquinolines and subsequent arylation or amination of the 2-aryl-3-(alkynyl)-4-chloroquinolines. Tetrahedron 66:8261–8266
Borah HN, Prajapati D, Boruah RC (2005) A novel indium-catalyzed Sonogashira coupling reaction, effected in the absence of a copper salt, phosphine ligand and palladium. Synlett, 2823–2825
Nishihara Y, Inoue E, Okada Y, Takagi K (2008) Sila-Sonogashira cross-coupling reactions of activated aryl chlorides with alkynylsilanes. Synlett, 3041–3045
Gelman D, Buchwald SL (2003) Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: use of a copper cocatalyst inhibits the reaction. Angew Chem Int Ed 42:5993–5996
Choy PY, Chow WK, So CM, Lau CP, Kwong FY (2010) Palladium-catalyzed Sonogashira coupling of aryl mesylates and tosylates. Chem Eur J 16:9982–9985
R’kyek O, Halland N, Lindenschmidt A, Alonso J, Lindemann P, Urmann M, Nazaré M (2010) A general palladium-catalyzed Sonogashira coupling of aryl and heteroaryl tosylates. Chem Eur J 16:9986–9989
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Noyori, S., Nishihara, Y. (2013). Recent Advances in Cross-Coupling Reactions with Aryl Chlorides, Tosylates, and Mesylates. In: Nishihara, Y. (eds) Applied Cross-Coupling Reactions. Lecture Notes in Chemistry, vol 80. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-32368-3_7
Download citation
DOI: https://doi.org/10.1007/978-3-642-32368-3_7
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-32367-6
Online ISBN: 978-3-642-32368-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)