Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride

Undercover agents: The biaryl coupling of an aryltrifluoroborate with an aryl bromide involves in situ hydrolysis of the boron reagent. The hydrolysis products are key components in ensuring that the reaction proceeds with high efficiency and avoids the extensive generation of undesired phenolic and...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2010-07, Vol.49 (30), p.5156-5160
Main Authors: Butters, Mike, Harvey, Jeremy N, Jover, Jesus, Lennox, Alastair J.J, Lloyd-Jones, Guy C, Murray, Paul M
Format: Article
Language:English
Subjects:
Borates - chemistry
boron
Boronic Acids - chemistry
fluorides
Fluorides - chemistry
Fluorine Compounds - chemistry
homogeneous catalysis
Molecular Structure
palladium
reaction mechanisms
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Summary:Undercover agents: The biaryl coupling of an aryltrifluoroborate with an aryl bromide involves in situ hydrolysis of the boron reagent. The hydrolysis products are key components in ensuring that the reaction proceeds with high efficiency and avoids the extensive generation of undesired phenolic and homocoupling side products.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201001522