Abstract
Arylation, vinylation and alkylation of a wide range of NH/OH/SH substrates by oxidative cross-coupling with boronic acids in the presence of catalytic cupric acetate, weak base and in air (open-flask chemistry).
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(a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahe dron Lett. 1998, 39, 2933-2936. (b) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tet rahedron Lett. 1998, 39, 2941-2949. Dominic Chan is a chemist at DuPont Crop Protection, Wilming ton, DE, USA. He did his PhD research with Prof. Barry Trost at the University of Wisconson, Madison. Patrick Lam is a research director at Bristol–Myers Squibb, Princeton, NJ, USA. He was formerly with DuPont Pharmaceuticals Company. He did his PhD research with Prof. Louis Friedrich in the Univeristy of Rochester and Post-doc research with Prof. Michael Jung and the late Prof. Don ald Cram in UCLA. (c) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940. Prof. Evans’ group found out about the discovery of this reaction on a National Organic Symposium poster and became interested in the O-arylation because of his long interest in vancomycin total synthesis. (d) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Averill, K. M.; Chan, D. M. T.; Combs, A. Synlett 2000, 674-676. (e) Lam, P. Y. S.; Bonne, D.; Vincent, G.; Clark, C. G.; Combs, A. P. Tetrahedron Lett. 2003, 44, 1691-1694.
Reviews: (a) Qiao, J. X.; Lam, P. Y. S. Syn. 2011, 829-856; (b) Chan, D. M. T.; Lam, P. Y. S., Book chapter in Boronic Acids Hall, ed. 2005, Wiley–VCH, 205–240. (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. Engl. 2003, 42, 5400–5449.
Catalytic copper: (a) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418. (b) Antilla, J. C.; Buch wald, S. L. Org. Lett. 2001, 3, 2077-2079. (c) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397-4400. (d) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236. (e) Lan, J.-B.; Zhang, G.-L.; Yu, X.-Q.; You, J.-S.; Chen, L.; Yan, M.; Xie, R.-G. Synlett 2004, 1095-1097.
Mechanism (Part of the mechanistic work from Shannon’s lab was funded and in collaboration with BMS: (a) Huffman, L. M.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 9196-9197. (b) King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044. (c) King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068-12073. (d) Casita, A.; King, A. E.; Prella, T.; Costas, M.; Stahl, S. S.; Ribas, X. J. Chem. Sci. 2010, 1, 326-330.
Vinyl boronic acids: Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahe dron Lett. 2003, 44, 4927-4931.
Intramolecular: Decicco, C. P.; Song, Y.; Evans, D.A. Org. Lett. 2001, 3, 1029-1032.
Solid phase: (a) Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahe dron Lett. 1999, 40, 1623-1626. (b) Combs, A. P.; Tadesse, S.; Rafalski, M.; Haque, T. S.; Lam, P. Y. S. J. Comb. Chem. 2002, 4, 179-182.
Boronates/borates: (a) Chan, D. M. T.; Monaco, K. L.; Li, R.; Bonne, D.; Clark, C. G.; Lam, P. Y. S. Tetrahedron Lett. 2003, 44, 3863-3865. (b) Yu, X. Q.; Yamamoto, Y.; Miyuara, N. Chem. Asian J. 2008, 3, 1517-1522.
Siloxanes: (a) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600-7601. (b) Lam, P. Y. S.; Deudon, S.; Hauptman, E.; Clark, C. G. Tetrahedron Lett. 2001, 42, 2427-2429.
Stannanes: Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2002, 43, 3091-3094.
Thiols: (a) Herradura, P. S.; Pendora, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. (b) Savarin, C.; Srogl, J.; Liebeskind, L. S. . Org. Lett. 2002, 4, 4309-4312. (c) Xu, H.-J.; Zhao, Y.-Q.; Feng, T.; Feng, Y.-S. J. Org. Chem. 2012, 77, 2878-2884.
Sulfinates: (a) Beaulieu, C.; Guay. D.; Wang, C.; Evans, D. A. Tetrahedron Lett. 2004, 45, 3233-3236. (b) Huang, H.; Batey, R. A. Tetrahedron. 2007, 63, 7667-7672. (c) Kar, A.; Sayyed, L.A.; Lo, W.F.; Kaiser, H.M.; Beller, M.; Tse, M. K. Org. Lett. 2007, 9, 3405-3408.
Sulfoximines: Moessner, C.; Bolm, C. Org. Lett. 2005, 7, 2667-2669.
β-Lactam: Wang, W.; et al. Bio. Med. Chem. Lett. 2008, 18, 1939-1944.
Cyclopropyl boronic acid: Tsuritani, T.; Strotman, N. A.; Yamamoto, Y.; Kawasaki, M.; Yasuda, N.; Mase, T. Org. Lett. 2008, 10, 1653-1655.
Alcohols: Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381-1384.
Fluorides: (a) Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2013, 135, 4648-4651. (b) Fier, P. S.; Luo, J.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2552-2559.
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Li, J.J. (2014). Chan–Lam C–X coupling reaction. In: Name Reactions. Springer, Cham. https://doi.org/10.1007/978-3-319-03979-4_56
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