Abstract
Aldehydes obtained from olefins under hydroformylation conditions can be converted to more complex reaction products in one-pot reaction sequences. These involve heterofunctionalization of aldehydes to form acetals, aminals, imines and enamines, including reduction products of the latter in an overall hydroaminomethylation. Furthermore, numerous conversions of oxo aldehydes with additional C,C-bond formation are conceivable such as aldol reactions, allylations, carbonyl olefinations, ene reactions and electrophilic aromatic substitutions, including Fischer indole syntheses.
Access provided by Autonomous University of Puebla. Download to read the full chapter text
Chapter PDF
Similar content being viewed by others
References
Bohnen HW, Cornils B (2002) Adv Catal 47:1
Cornils B (1999) J Mol Catal A-Chem 143:1
Beller M, Cornils B, Frohning CD, Kohlpaintner CW (1995) J Mol Catal A-Chem 104:17
Cornils B, Herrmann WA, Kohlpaintner CW (1994) Angew Chem Int Ed Engl 33:2144
Cornils B, Herrmann WA (1996) Applied Homogeneous Catalysis with Organometallic Compounds. Wiley-VCH, Weinheim
van Leeuwen PWNM, Claver C (2000) Rhodium-Catalyzed Hydroformylation. Kluwer, Dordrecht
Burke SD, Cobb JE, Takeuchi K (1990) J Org Chem 55:2138
Breit B, Zahn SK (1998) Tetrahedron Lett 39:1901
Hornberger KR, Hamblett CL, Leighton JL (2000) J Am Chem Soc 122:12894
Breit B (2000) Chem Eur J 6:1519
Dreher SD, Leighton JL (2001) J Am Chem Soc 123:341
Liu P, Jacobsen EN (2001) J Am Chem Soc 123:10772
Breit B, Zahn SK (2001) J Org Chem 66:4870
Sun P, Sun C, Weinreb SM (2001) Org Lett 3:3507
Sun P, Sun CX, Weinreb SM (2002) J Org Chem 67:4337
Seepersaud M, Kettunen M, Abu-Surrah AS, Repo T, Voelter W, Al-Abed Y (2002) Tetrahedron Lett 43:1793
Weinreb SM (2003) Acc Chem Res 36:590
Gladiali S, Bayon JC, Claver C (1995) Tetrahedron: Asymmetry 6:1453
Eilbracht P (1995) In: Helmchen G, Hoffmann RW, Mulzer J (eds) Methoden der Organischen Chemie (Houben-Weyl), vol E 21c. Thieme, Stuttgart, p 2488
Agbossou F, Carpentier JF, Mortreux A (1995) Chem Rev 95:2485
Breit B, Seiche W (2001) Synthesis, p 1
Breit B (2003) Acc Chem Res 36:264
Patai S (1970) The Chemistry of the Carbonyl Group. Wiley, New York
Falbe J (1983) Methoden der Organischen Chemie (Houben-Weyl), vol E3. Thieme, Stuttgart
Tietze LF (1996) Chem Rev 96:115
Fogg DE, dos Santos EN (2003) Coord Chem Rev 284:2365
Eilbracht P, Bärfacker L, Buss C, Hollmann C, Kitsos-Rzychon B, Kranemann CL, Rische T, Roggenbuck R, Schmidt A (1999) Chem Rev 99:3329
Schmidt AM, Eilbracht P (2004) New Synthetic Applications of Tandem Reactions under Hydroformylation Conditions. In: Beller M, Bolm C (eds) Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Wiley, Weinheim, p 57
Schmidt AM, Eilbracht P (2004) Multiple Carbon-Carbon Bond Formations under Hydroformylation Conditions. In: Beller M, Bolm C (eds) Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Wiley, Weinheim, p 87
Parsons PJ, Penkett CS, Shell AJ (1996) Chem Rev 96:195
Nicolaou KC, Montagnon T, Snyder SA (2003) Chem Commun, p 551
Wuts PGM, Obrzut ML, Thompson PA (1984) Tetrahedron Lett 25:4051
Schmidt B, Costisella B, Roggenbuck R, Westhus M, Wildemann H, Eilbracht P (2001) J Org Chem 66:7658
Roggenbuck R, Schmidt A, Eilbracht P (2002) Org Lett 4:289
Ojima I, Moralee AC, Vassar VC (2002) Top Catal 19:89
Ojima I, Vidal ES (1998) J Org Chem 63:7999
Ojima I, Tzamarioudaki M, Eguchi M (1995) J Org Chem 60:7078
Eguchi M, Zeng Q, Korda A, Ojima I (1993) Tetrahedron Lett 34:915
Ojima I, Iula DM (1998) In: Pelletier SW (ed) The Alkaloids. Pergamon, London, p 371
Mizutani N, Chiou WH, Ojima I (2002) Org Lett 4:4575
Dixon DJ, Horan RAJ, Monck NJT (2004) Org Lett 6:4423
Bergmann DJ, Campi EM, Jackson WR, Patti AF (1999) Chem Commun, p 1279
Bergmann DJ, Campi EM, Jackson WR, Patti AF (1999) Aust J Chem 52:1131
Bergmann DJ, Campi EM, Jackson WR, Patti AF, Saylik D (1999) Tetrahedron Lett 40:5597
Campi EN, Jackson WR, McCubbin QJ, Trnacek AE (1994) Aust J Chem 47:1061
Campi EN, Jackson WR, Trnacek AE (1997) Aust J Chem 50:1031
Dong Y, Busacca CA (1997) J Org Chem 62:6464
Ucciani E, Bonfand AJ (1981) Chem Soc Chem Commun, p 82
Cannon JG (1981) J Med Chem 24:238
Siu J, Baxendale IR, Ley SV (2004) Org Biomol Chem 2:160
Douglas AW (1994) Tetrahedron Lett 35:6807
Teoh E, Campi EM, Jackson WR (2002) Chem Commun, p 978
Teoh E, Campi EM, Jackson WRN, Robinson AJ (2003) New J Chem 27:387
Teoh E, Jackson WR, Robinson AJ (2005) Aust J Chem 58:63
Botteghi C, Cazzolato L, Marchetti M, Paganelli S (1995) J Org Chem 60:6612
Rische T, Eilbracht P (1999) Tetrahedron 55:1915
Rische T, Müller KS, Eilbracht P (1999) Tetrahedron 55:9801
Botteghi C, Corrias T, Marchetti M, Paganelli S, Piccolo O (2002) Org Proc Res Develop 6:379
Donsbach M, Eilbracht P, Buss C, Mersch C (2000) DE 10033016 A1
Kranemann CL, Costisella B, Eilbracht P (1999) Tetrahedron Lett 40:7773
Kranemann CL, Eilbracht P (2000) Eur J Org Chem 2367
Angelovski G, Eilbracht P (2003) Tetrahedron 41:8265
Angelovski G, Costisella B, Kolaric B, Engelhard M, Eilbracht P (2004) J Org Chem 69:5290
Koç K, Eilbracht P (2004) Tetrahedron 60:8465
Koc F, Wyszogrodzka M, Eilbracht P, Haag R (2005) J Org Chem 70:2021
Jachimowicz F, Hansson A (1985) In: Augustine RL (ed) Catalysis of Organic Reactions. Dekker, New York, p 381
Jachimowicz F, Hansson A (1988) Can Patent 1231199
Jachimowicz F (1981) GE 3106139
Sunder A, Turk H, Haag R, Frey H (2000) Macromolecules 33:7682
Cornils B (1980) In: Falbe J (ed) New Syntheses with Carbon Monoxide. Springer, Berlin Heidelberg New York, p 1
Kranemann CL, Eilbracht P (1998) Synthesis, p 71
Bärfacker L (1999) Thesis, Dortmund University
Bärfacker L, Eilbracht P, personal communication
Zacuto MJ, Leighton JL (2000) J Am Chem Soc 122:8587
O'Malley SJ, Leighton JL (2001) Angew Chem Int Ed 40:2915
Dreher SD, Leighton JL (2001) J Am Chem Soc 123:341
Zacuto MJ, O'Malley SJ, Leighton JL (2002) J Am Chem Soc 124:7890
Hoffmann RW, Brückner D, Gerusz VJ (2000) Heterocycles 52:121
Hoffmann RW, Brückner D (2001) New J Chem 25:369
Hoffmann RW, Kruüger J, Brückner D (2001) New J Chem 25:102
Dessole G, Marchetti M, Taddei MJ (2003) Comb Chem 5:198
Settambolo R, Savi S, Caiazzo A, Lazzaroni RJ (2000) Organomet Chem 601:320
Settambolo R, Caiazzo A, Lazzaroni R (2001) Tetrahedron Lett 42:4045
Settambolo R, Savi S, Caiazzo A, Lazzaroni RJ (2001) Organomet Chem 619:241
Hollmann C, Eilbracht P (1999) Tetrahedron Lett 40:4313
Hollmann C, Eilbracht P (2000) Tetrahedron 56:1685
Hollmann C (2000) Thesis, Dortmund University
Keränen MD, Hollmann C, Kot K, Eilbracht P (2004) Org Biomol Chem 2:3379
Keränen MD, Eilbracht P (2004) Org Biomol Chem 2:1688
Diaz AO, Augusti R, dos Santos EN, Gusevskaya EV (1997) Tetrahedron Lett 38:41
Roggenbuck R, Eilbracht P (1999) Tetrahedron Lett 40:7455
Köhling P, Schmidt AM, Eilbracht P (2003) Org Lett 5:3213
Ahmed M, Jackstell R, Seayad AM, Klein H, Beller M (2004) Tetrahedron Lett 45:869
Schmidt AM, Eilbracht P (2005) Org Biomol Chem 3:233
Köhling P, Schmidt AM, Eilbracht P (2006) Org Biomol Chem 4:302
Schmidt AM, Eilbracht P (2005) J Org Chem 70:5528
Schmidt AM (2005) Thesis, Dortmund University
Schmidt AM, Eilbracht P (2005) personal communication
Author information
Authors and Affiliations
Corresponding author
Editor information
Rights and permissions
Copyright information
© 2006 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Eilbracht, P., Schmidt, A.M. (2006). Synthetic Applications of Tandem Reaction Sequences Involving Hydroformylation. In: Beller, M. (eds) Catalytic Carbonylation Reactions. Topics in Organometallic Chemistry, vol 18. Springer, Berlin, Heidelberg . https://doi.org/10.1007/3418_017
Download citation
DOI: https://doi.org/10.1007/3418_017
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-33002-8
Online ISBN: 978-3-540-33003-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)