Abstract
N-Heterocyclic carbenes (NHCs) are widely used as ligands in catalysis by transition metal complexes. The catalytic activity of transition metal NHC complexes is much higher than that of the transition metal complexes bearing the phosphine and nitrogen-containing ligands. They show excellent catalytic performance in different transformations of the organic compounds, especially in the carbon—carbon and carbon—element bond forming reactions. Palladium NHC complexes are very efficient catalysts for the cross-coupling reactions. On the other hand, nickel is less expensive and regarded as a promising alternative to palladium and, therefore, it attracts increasing attention from the researches. The present review is focused on the recent advances in the synthesis of N-heterocyclic carbene complexes of nickel and palladium and their application in catalysis of cross-coupling reactions of organic, organoelement and organometallic compounds with organic halides.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
L. Mercs, M. Albrecht, Chem. Soc. Rev., 2010, 39, 1903.
S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev., 2009, 109, 3612.
M. Poyatos, J. A. Mata, E. Peris, Chem. Rev., 2009, 109, 3677.
D. S. McGuinness, K. J. Cavell, B. W. Skelton, A. H. White, Organometallics, 1999, 18, 1596.
K. Inamoto, J. Kuroda, T. Sakamoto, K. Hiroya, Synthesis, 2007, 2853.
C. C. Lee, W. C. Ke, K. T. Chan, C. L. Lai, C. H. Hu, H. M. Lee, Chem. Eur. J., 2007, 13, 582.
Z. X. Xi, X. M. Zhang, W. Z. Chen, S. Z. Fu, D. Q. Wang, Organometallics, 2007, 26, 6636.
P. L. Chiu, C. L. Lai, C. F. Chang, C. H. Hu, H. M. Lee, Organometallics, 2005, 24, 6169.
J. Wolf, A. Labande, J. C. Daran, R. Poli, J. Organomet. Chem., 2006, 691, 433.
S. K. Schneider, C. F. Rentzsch, A. Krueger, H. G. Raubenheimer, W. A. Herrmann, J. Mol. Catal. A: Chem., 2007, 265, 50.
Z. X. Xi, Y. B. Zhou, W. Z. Chen, J. Org. Chem., 2008, 73, 8497.
A. P. Prakasham, P. Ghosh, Inorg. Chim. Acta, 2015, 431, 61.
S. Gu, C. Chen, H. Qiu, W. Chen, Curr. Org. Chem., 2011, 15, 3291.
A. J. Arduengo III, H. V. R. Dias, R. L. M. Harlow, J. Am. Chem. Soc., 1992, 114, 5530.
C. Zhang, Z.-X. Wang, Organometallics, 2009, 28, 6507.
Y. Kong, M. Cheng, H. Ren, S. Xu, H. Song, M. Yang, B. Liu, B. Wang, Organometallics, 2011, 30, 1677.
K. Zhing, M. Conda-Sheridan, S. R. Cooke, J. Louie, Organometallics, 2011, 30, 2546.
C. A. Laskowski, A. J. Miller, G. L. Hillhouse, T. R. Cundari, J. Am. Chem. Soc., 2011, 133, 771.
C.-Y. Liao, K.-T. Chan, J.-Y. Zeng, C.-H. Hu, C.-Y. Tu, H. M. Lee, Organometallics, 2007, 26, 1692.
F. J.-B. dit Dominique, H. Gornitzka, C. Hemmert, Organometallics, 2010, 29, 2868.
A. V. Astakhov, O. V. Khazipov, E. S. Degtyareva, V. N. Khrustalev, V. M. Chernyshev, V. P. Ananikov, Organometallics, 2015, 34, 5759.
T. Steinke, B. K. Shaw, H. Jong, B. O. Patrick, M. D. Fryzuk, Organometallics, 2009, 28, 2830.
D. S. McGuinness, K. J. Cavell, B. F. Yates, B. W. Skelton, A. H. White, J. Am. Chem. Soc., 2001, 123, 8317.
A. Fürstner, G. Seidel, D. Kremzow, C. W. Lehmann, Organometallics, 2003, 22, 907.
D. Kremzow, G. Seidel, C. W. Lehmann, A. Fürstner, Chem. Eur. J., 2005, 11, 1833.
A. J. Arduengo III, D. Tapu, W. J. Marshall, J. Am. Chem. Soc., 2005, 127, 16400.
H. M. J. Wang, I. J. B. Lin, Organometallics, 1998, 17, 972.
S. Wang, F. Ren, Y. Qiu, M. Luo, J. Organomet. Chem., 2015, 788, 27.
Y.-H. Chang, Z.-Y. Liu, Y.-H. Liu, S.-M. Peng, J.-T. Chen, S.-T. Liu, Dalton Trans., 2011, 40, 489.
P. V. Simpson, B. W. Skelton, D. H. Brown, M. V. Baker, Eur. J. Inorg. Chem., 2011, 1937.
Y. Zhou, Z. Xi, W. Chen, Organometallics, 2008, 27, 5911.
D. Baskakov, W. A. Herrmann, E. Herdtweck, S. D. Hoffmann, Organometallics, 2007, 26, 626.
B. Liu, X. Liu, Ch. Chen, C. Chen, W. Chen, Organometallics, 2012, 31, 282.
B. Liu, Y. Zhang, D. Xu, W. Chen, Chem. Commun., 2011, 47, 2883.
M. R. Chaulagain, G. M. Mahandru, J. Montgomery, Tetrahedron, 2006, 62, 7560.
R. A. Kelly, N. M. Scott, S. Diez-Gonzalez, E. D. Stevens, S. P. Nolan, Organometallics, 2005, 24, 3442.
M. A. Selepe, F. R. V. Heerden, Molecules, 2013, 18, 4739.
S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron, 2002, 58, 9633.
S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem., Int. Ed., 2001, 40, 4544.
S. S. Gujral, S. Khatri, P. Riyal, V. Gahlot, Indo Global. J. Pharm. Sci., 2012, 2, 351.
D. Astruc, Anal. Bioanal. Chem., 2011, 399, 1811.
X. F. Wu, P. Anbarasan, H. Neumann, M. Beller, Angew. Chem., Int. Ed., 2010, 49, 9047.
F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron, 2008, 64, 3047.
R. Martin, S. L. Buchwald, Acc. Chem. Res., 2008, 41, 1461.
F. Bellina, A. Carpita, R. Rossi, Synthesis, 2004, 15, 2419.
N. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457.
C. Valente, S. Calimsiz, K. H. Hoi, D. Mallik, M. Sayah, M. G. Organ, Angew. Chem., Int. Ed., 2012, 51, 3314.
G. C. Fortman, S. P. Nolan, Chem. Soc. Rev., 2011, 40, 5151.
N. Muthukumaran, P. Govindan, R. Rangasamy, V. Periasamy, M. J. Grzegorz, L. Wolfgang, J. Mol. Catal. A: Chem., 2015, 397, 56.
L. Luconi, Z. N. Gafurov, A. Rossin, G. Tuci, O. G. Sinyashin, D. G. Yakhvarov, G. Giambastiani, Inorg. Chim. Acta, 2018, 470, 100.
F. S. Han, Chem. Soc. Rev., 2013, 42, 5270.
K. Inamoto, J.-I. Kuroda, E. Kwon, K. Hiroya, T. Doi, J. Organomet. Chem., 2009, 694, 389.
K. Inamoto, J.-I. Kuroda, K. Hiroya, Y. Noda, M. Watanabe, T. Sakamoto, Organometallics, 2006, 25, 3095.
T. Tu, H. Mao, C. Herbert, M. Xu, K. H. Dötz, Chem. Commun., 2010, 46, 7796.
M. Xu, X. Li, Z. Sun, T. Tu, Chem. Commun., 2013, 49, 11539.
A. S. Sigeev, A. S. Peregudov, A. V. Cheprakov, I. P. Beletskaya, Adv. Synth. Catal., 2015, 357, 417.
A. N. Kashin, O. G. Ganina, A. V. Cheprakov, I. P. Beletskaya, ChemCatChem, 2015, 7, 2113.
S. Iyer, A. Jayanthi, Synlett, 2003, 1125.
J. Zhou, G. C. Fu, J. Am. Chem. Soc., 2003, 125, 12527.
N. Hadei, E. A. B. Kantchev, C. J. O´Brien, M. G. Organ, Org. Lett., 2005, 7, 3805.
I. D. Hills, M. R. Netherton, G. C. Fu, Angew. Chem., Int. Ed., 2003, 115, 5927.
X. M. Zhang, Z. X. Xi, A. L. Liu, W. Z. Chen, Organometallics, 2008, 27, 4401.
X. M. Zhang, A. L. Liu, W. Z. Chen, Org. Lett., 2008, 10, 3849.
J. S. Ye, W. Z. Chen, D. Q. Wang, Dalton Trans., 2008, 4015.
D. S. McGuinness, K. J. Cavell, Organometallics, 2000, 19, 741.
S. Grundemann, M. Albrecht, J. A. Loch, J. W. Faller, R. H. Crabtree, Organometallics, 2001, 20, 5485.
E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun., 2001, 201.
J. A. Loch, M. Albrecht, E. Peris, J. Mata, J. W. Faller, R. H. Crabtree, Organometallics, 2002, 21, 700.
M. Yus, I. M. Pastor, Chem. Lett., 2013, 42, 94.
A.-L. Lee, Annu. Rep. Prog. Chem., Sect. B: Org. Chem., 2009, 105, 421.
A. V. Astakhov, O. V. Khazipov, A. Yu. Chernenko, D. V. Pasyukov, A. S. Kashin, E. G. Gordeev, V. N. Khrustalev, V. M. Chernyshev, V. P. Ananikov, Organometallics, 2017, 36, 1981.
K. Inamoto, J. Kuroda, T. Danjo, T. Sakamoto, Synlett, 2005, 1624.
T. A. P. Paulose, S. C. Wu, J. A. Olson, T. Chau, N. Theaker, M. Hassler, J. W. Quail, S. R. Foley, Dalton Trans., 2012, 41, 251.
J. Huang, S. P. Nolan, J. Am. Chem. Soc., 1999, 121, 9889.
V. P. W. Böhm, T. Weskamp, C. W. K. Gstottmayr, W. A. Herrmann, Angew. Chem., Int. Ed., 2000, 39, 1602.
V. P. W. Böhm, C. W. K. Gstottmayr, T. Weskamp, W. A. Herrmann, Angew. Chem., Int. Ed., 2001, 40, 3387.
A. C. Frisch, F. Rataboul, A. Zapf, M. Beller, J. Organomet. Chem., 2003, 687, 403.
M. G. Organ, M. Abdel-Hadi, S. Avola, N. Hadei, J. Nasielski, C. J. O´Brien, C. Valente, Chem. Eur. J., 2007, 13, 150.
A. C. Frisch, A. Zapf, O. Briel, B. Kayser, N. Shaikh, M. Beller, J. Mol. Catal., 2004, 214, 231.
C. Chen, H. Qiu, W. Chen, J. Organomet. Chem., 2012, 696, 4166.
K. Matsubara, K. Ueno, Y. Shibata, Organometallics, 2006, 25, 3422.
S. J. Gu, W. Z. Chen, Organometallics, 2009, 28, 909.
A. L. Liu, X. M. Zhang, W. Z. Chen, Organometallics, 2009, 28, 4868.
C. B. Kim, H. Jo, B. K. Ahn, C. K. Kim, K. Park, J. Org. Chem., 2009, 74, 9566.
H. V. Huynh, R. Jothibasu, Eur. J. Inorg. Chem., 2009, 1926.
J. Berding, M. Lutz, A. L. Spek, E. Bouwman, Organometallics, 2009, 28, 1845.
J. Berding, T. F. van Dijkman, M. Lutz, A. L. Spek, E. Bouwman, Dalton Trans., 2009, 6948.
S. Miyazaki, Y. Koga, T. Matsumoto, K. Matsubara, Chem. Commun., 2010, 46, 1932.
G. Manolikakes, N. Dastbaravardeh, P. Knochel, Synlett, 2007, 2077.
A. Leleu, Y. Fort, R. Schneider, Adv. Synth. Catal., 2006, 348, 1086.
K. Matsubara, K. Ueno, Y. Koga, K. J. Hara, J. Org. Chem., 2007, 72, 5069.
H. V. Huynh, L. R. Wong, P. S. Ng, Organometallics, 2008, 27, 2231.
T. Zell, P. Fischer, D. Schmidt, U. Radius, Organometallics, 2012, 31, 5065.
L. Jiang, S. L. Buchwald, Metal-Catalyzed Cross-Coupling Reactions, Eds A. de Meijere, F. Diederich, 2nd ed., 2004, Wiley-VCH Verlag, Weinheim, p. 699.
Q. Shen, J. F. Hartwig, J. Am. Chem. Soc., 2006, 128, 10028.
J. C. Green, B. J. Herbert, R. Lonsdale, J. Organomet. Chem., 2005, 690, 6054.
S. Caddick, F. G. N. Cloke, P. B. Hitchcock, J. Leonard, A. K. De K. Lewis, D. McKerrecher, L. R. Titcomb, Organometallics, 2002, 21, 4318.
A. K. de K. Lewis, S. Caddick, F. G. N. Cloke, N. C. Billingham, P. B. Hitchcock, J. Leonard, J. Am. Chem. Soc., 2003, 125, 10066.
M. S. Viciu, R. M. Kissling, E. D. Stevens, S. P. Nolan, Org. Lett., 2002, 4, 2229.
M. S. Viciu, R. A. Kelly III, E. D. Stevens, F. Naud, M. Studer, S. P. Nolan, Org. Lett., 2003, 5, 1479.
N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott, S. P. Nolan, J. Am. Chem. Soc., 2006, 128, 4101.
M. S. Viciu, R. F. Germaneau, O. Navarro-Fernandez, E. D. Stevens, S. P. Nolan, Organometallics, 2002, 21, 5470.
O. Navarro, N. Marion, N. M. Scott, J. Gonzalez, D. Amoroso, A. Bell, S. P. Nolan, Tetrahedron, 2005, 61, 9716.
B. Gradel, E. Brenner, R. Schneider, Y. Fort, Tetrahedron Lett., 2001, 42, 5689.
C. Desmarets, R. Schneider, Y. Fort, J. Org. Chem., 2002, 67, 3029.
S. Kuhl, Y. Fort, R. Schneider, J. Organomet. Chem., 2005, 690, 6169.
R. Omar-Amrani, A. Thomas, E. Brenner, R. Schneider, Y. Fort, Org. Lett., 2003, 5, 2311.
C. Chen, L. M. Yang, J. Org. Chem., 2007, 72, 6324.
C.-Y. Gao, L.-M. Yang, J. Org. Chem., 2008, 73, 1624.
K. Matsubara, S. Miyazaki, Y. Koga, Y. Nibu, T. Hashimura, T. Matsumoto, Organometallics, 2008, 27, 6020.
M. Tobisu, T. Shimasaki, N. Chatani, Chem. Lett., 2009, 38, 710.
T. Shimasaki, M. Tobisu, N. Chatani, Angew. Chem., Int. Ed., 2010, 49, 2929.
E. S. Degtyareva, J. V. Burykina, A. N. Fakhrutdinov, E. G. Gordeev, V. N. Khrustalev, V. P. Ananikov, ACS Catal., 2015, 5, 7208.
G. Bastug, S. P. Nolan, J. Org. Chem., 2013, 78, 9303.
E. Brachet, J. D. Brion, M. Alami, S. Messaoudi, Chem. Eur. J., 2013, 19, 15276.
M. J. Iglesias, A. Prieto, M. C. Nicasio, Adv. Synth. Catal., 2010, 352, 1949.
F.-J. Guoa, J. Suna, Z.-Q. Xub, F. E. Kьhnc, S.-L. Zanga, M.-D. Zhou, Catal. Commun., 96, 11.
Y. G. Zhang, K. C. Ngeow, J. Y. Ying, Org. Lett., 2007, 9, 3495.
G. U. Shaojin, N. I. Peng, C. Wanzhi, Chin. J. Catal., 2010, 31, 875.
E. A. B. Kantchev, C. J. O´Brien, M. G. Organ, Angew. Chem., Int. Ed., 2007, 46, 2768.
E. V. Bellan, A. I. Poddel´sky, N. A. Protasenko, A. V. Cherkasov, A. S. Bogomyakov, V. K. Cherkasov, G. A. Abakumov, Inorg. Chem. Commun., 2014, 50, 1
A. I. Poddel´sky, V. K. Cherkasov, G. A. Abakumov, Coord. Chem. Rev., 2009, 253, 291.
V. K. Cherkasov, G. A. Abakumov, E. V. Grunova, A. I. Poddel´sky, G. K. Fukin, E. V. Baranov, Yu. A. Kurskii, L. G. Abakumova, Chem. Eur. J., 2006, 12, 3916.
E. V. Ilyakina, A. I. Poddel´sky, V. K. Cherkasov, G. A. Abakumov, Mendeleev Commun., 2012, 22, 208.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences G. A. Abakumov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1529—1535, September, 2017.
Rights and permissions
About this article
Cite this article
Gafurov, Z.N., Kantyukov, A.O., Kagilev, A.A. et al. Nickel and palladium N-heterocyclic carbene complexes. Synthesis and application in cross-coupling reactions. Russ Chem Bull 66, 1529–1535 (2017). https://doi.org/10.1007/s11172-017-1920-7
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-017-1920-7