A Bicyclic N-Heterocyclic Carbene as a Bulky but Accessible Ligand: Application to the Copper-Catalyzed Borylations of Aryl Halides

Shin Ando*, Hirofumi Matsunaga and Tadao Ishizuka*

*Faculty of Life Sciences, Kumamoto University, 5-1 Oe-honmachi Chuo-ku, Kumamoto 862-0973, Japan, Email: andogpo.kumamoto-u.ac.jp, tstonegpo.kumamoto-u.ac.jp

S. Ando, H. Matsunaga, T. Ishizuka, J. Org. Chem., 2015, 80, 9671-9681.

DOI: 10.1021/acs.joc.5b01721

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Abstract

A well-defined bicyclic NHC-CuCl complex was successfully applied to copper-catalyzed borylations of aryl halides at ambient temperature. This bicyclic NHC-CuCl compex proved to be a suitable catalyst particularly for sterically hindered substrates, which suggested that the bicyclic NHC ligand offered a bulky but accessible environment to the bound copper.

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Key Words

aryl boronates

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ID: J42-Y2015