Organic Chemistry, Poster
OC-118

Gold-Catalyzed Oxidative C-H Arylation with Organoboron Reagents

A. Genoux1, M. Hofer1, R. Kumar1, C. Nevado1
1University of Zurich

Direct C(sp2)-H functionalization/arylation has attracted increasing interest since the substrates do not need to be functionalized in contrast to classical cross-coupling reactions.1 Despite significant progress,2 multiple challenges including low reactivity, lack of selectivity in the activation of an specific C(sp2)-H bonds and formation of homocoupling products (Ar1Ar1, Ar2Ar2) are still difficult to master.3 Herein, we report an efficient synthesis of biaryl compounds through a gold-catalyzed oxidative cross-coupling of arenes with strong electron-deprived aryl boronates. Non-symmetric biaryls can be synthesized with high levels of regio- and chemoselectivity under additives and directing groups-free conditions.This methodology shows orthogonal reactivity and complementary scope with respect to already existing methods.5

[1] a) X.-F. Wu, P. Anbarasan, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2010, 49, 9047; b) C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 2012, 51, 5062.
[2] a) D.-H. Wang, T.-S. Mei, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 17676; b) S. Yang,B.Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 6066; c) J. Norinder,A. Matsumoto, N.Yoshikai, E. Nakamura, J. Am. Chem. Soc. 2008, 130,5858; d) F. Kakiuchi, Y. Matsuura, S. Kan, N. Chatani, J. Am. Chem. Soc. 2005, 127, 5936.
[3] a) S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45,936; b) L. C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40,35.       
[4] M. Hofer, A. Genoux, R. Kumar, C. Nevado, Angew. Chem. Int. Ed. 2017, 56, 1021.
[5] a) L. T. Ball, G. C. Lloyd-Jones, C. A. Russell, Science 2012, 337, 1644; b) X. C. Cambeiro, N. Ahlsten, I. Larrosa, J. Am. Chem. Soc. 2015, 137, 15636.