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Iridium-Catalyzed CH Activation versus Directed ortho Metalation: Complementary Borylation of Aromatics and Heteroaromatics

✍ Scribed by Timothy E. Hurst; Todd K. Macklin; Maike Becker; Eduard Hartmann; Wolfgang Kügel; Jean-Christophe Parisienne-La Salle; Andrei S. Batsanov; Todd B. Marder; Victor Snieckus

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 272 KB
Volume: 16
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.201000401

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✦ Synopsis

Abstract

Systematic studies are presented demonstrating the complementarity of directed ortho metalation (D__o__M) and Ir‐catalyzed strategies for the provision of borylated aromatics and their subsequent Suzuki–Miyaura coupling reactions. A new concept, the use of the TMS group, readily introduced by D__o__M, as a latent regiodirective moiety to overcome the otherwise problematic production of isomeric borylated product mixtures is presented. Additional electrophile‐induced ipso‐deborylation and D__o__M reactions of the Bpin products are described.

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ChemInform Abstract: Iridium-Catalyzed C

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