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

被引：95

作者：

Hurst, Timothy E. ^{[1
]}

Macklin, Todd K. ^{[1
]}

Becker, Maike ^{[1
]}

Hartmann, Eduard ^{[1
]}

Kuegel, Wolfgang ^{[1
]}

Parisienne-La Salle, Jean-Christophe ^{[1
]}

Batsanov, Andrei S. ^{[2
]}

Marder, Todd B. ^{[2
]}

Snieckus, Victor ^{[1
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

[2] Univ Durham, Dept Chem, Durham DH1 3LE, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 27期

基金：

加拿大自然科学与工程研究理事会;

关键词：

boron; C-H activation; deborylation; metalation; Suzuki-Miyaura coupling; ONE-POT; BORONIC ACIDS; ARENES; FUNCTIONALIZATION; HETEROARENES; COMPLEXES; CHEMISTRY; ROUTE; MILD; HYDROCARBONS;

D O I：

10.1002/chem.201000401

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Systematic studies are presented demonstrating the complementarity of directed ortho metalation (DoM) 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 DoM, as a latent regiodirective moiety to overcome the otherwise problematic production of isomeric borylated product mixtures is presented. Additional electrophile-induced ipso-deborylation and DoM reactions of the Bpin products are described.

引用

页码：8155 / 8161

页数：7

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