Organic letters

Directed ortho-Metalation–Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides

C Schneider, E Broda, V Snieckus

Index: Schneider, Cedric; Broda, Ellen; Snieckus, Victor Organic Letters, 2011 , vol. 13, # 14 p. 3588 - 3591

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Citation Number: 21

Abstract

A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (D o M) and either MeOBPin or i-PrOBpin electrophile quench, 3→ 4, is described. A one-pot metalation–Suzuki cross-coupling procedure for the synthesis of biaryls and heterobiaryls, 3→ 5, and a complementary D o M–Ir-catalyzed boronation sequence (Scheme 6) are delineated.

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