A Direct, Chemo-, and Regioselective Cross-Coupling Reaction of Arenes via Sequential Directed ortho Cuprations and
Noriyuki Tezuka1,2, Keiichi Hirano1,2, Masanobu Uchiyama1,2,3
1Graduate School of Pharmaceutical Sciences , The University of Tokyo , 7-3-1 Hongo , Bunkyo-ku , Tokyo 113-0033 , Japan.
Abstract:
Direct cross-coupling of Csp2-H/Csp2-H bonds of two arenes was achieved in 30-76% yield via sequential directed ortho cuprations (DoCu) with the cuprate base (TMP)2Cu(CN)Li2 (1, TMP = 2,2,6,6-tetramethylpiperidido), followed by oxidation. This methodology offers easy access to unsymmetric biaryls from arenes with a variety of directed metalation groups (DMGs) and ancillary functional groups, taking advantage of the highly chemoselective action of 1.
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