Lam C-X coupling reaction

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 56, Springer International Publishing Switzerland 2014 

Vinyl boronic acids Lam, P. Y. S. Vincent, G. Bonne, D. Clark, C. G. Tetrahe dron Lett. 2003, 44,4927 931. 

Cyclopropyl boronic acid Tsuritani, T. Strotman, N. A. Yamamoto, Y. Kawa shki, M. Yasuda, N. Mase, T. Org. Lett 2008,10,1653-1655. 

Chapman, A. W. J. Cfera. 5oc. 1925, i27, 1992-1998. Arthur William Chapman was bom in 1898 in London, England. He was a Lecturer in Organic Chemistry and later became Registrar of the University of Sheffield from 1944 to 1963. 

Arylation of a wide range of NH/OH/SH substrates by oxidative cross-coupling with boronic acids in the presence of catalytic cupric acetate and either triethyl-amine or pyridine at room temperature in air. The reaction works for amides, amines, anilines, azides, hydantoins, hydrazines, imides, imines, nitroso, pyrazi-nones, pyridones, purines, pyrimidines, sulfonamides, sulfmates, sulfoximines, ureas, alcohols, phenols, and thiols. It is also the mildest method for NIO-vinylation. The boronic acids can be replaced with siloxanes or starmanes. The mild condition of this reaction is an advantage over Buchwald-Hartwig s Pd-catalyzed cross-coupling. The Chan-Lam C-X bond cross-coupling reaction is complementary to Suzuki-Miyaura s C-C bond cross-coupling reaction. 

Name Reactions, 4th ed., DOI 10.1007/978-3-642-01053-8 49, Springer-Verlag Berlin Heidelberg 2009 

93% (a-ester assistance, acetal lower yield, e.g., dimethyl acetal, 23%) 

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