Selection of boron reagents for Suzuki-Miyaura coupling

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...

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Bibliographic Details
Published in:Chemical Society reviews 2014-01, Vol.43 (1), p.412-443
Main Authors: Lennox, Alastair J. J, Lloyd-Jones, Guy C
Format: Article
Language:English
Subjects:
Bonding
Boron
Carbon-carbon composites
Chemical reactions
Cross coupling
Joining
Samarium
Transition metals
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Summary: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. This review analyses the general physical and chemical properties of the seven main classes of boron reagent that have been employed for SM coupling.
ISSN:0306-0012
1460-4744
DOI:10.1039/c3cs60197h