Issue 1, 2014

Selection of boron reagents for Suzuki–Miyaura coupling

Abstract

Suzuki–Miyaura (SM) cross-coupling is arguably the most widely-applied transition metal catalysed carbon–carbon bond forming reaction to date. Its success originates from a combination of exceptionally mild and functional group tolerant reaction conditions, with a relatively stable, readily prepared and generally environmentally benign organoboron reagent. A variety of such reagents have been developed for the process, with properties that have been tailored for application under specific SM coupling conditions. This review analyses the seven main classes of boron reagent that have been developed. The general physical and chemical properties of each class of reagent are evaluated with special emphasis on the currently understood mechanisms of transmetalation. The methods to prepare each reagent are outlined, followed by example applications in SM coupling.

Graphical abstract: Selection of boron reagents for Suzuki–Miyaura coupling

Article information

Article type
Review Article
Submitted
12 Jun 2013
First published
03 Oct 2013
This article is Open Access
Creative Commons BY license

Chem. Soc. Rev., 2014,43, 412-443

Selection of boron reagents for Suzuki–Miyaura coupling

A. J. J. Lennox and G. C. Lloyd-Jones, Chem. Soc. Rev., 2014, 43, 412 DOI: 10.1039/C3CS60197H

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