Boron: A key element in radical reactions

Boron derivatives are becoming key reagents in radical chemistry. Here, we describe reactions where an organoboron derivative is used as a radical initiator, a chain-transfer reagent, and a radical precursor. For instance, -alkylcatecholboranes, easily prepared by hydroboration of alkenes, represent...

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Published in:Pure and applied chemistry 2007-02, Vol.79 (2), p.223-233
Main Authors: Renaud, Philippe, Beauseigneur, Alice, Brecht-Forster, Andrea, Becattini, Barbara, Darmency, Vincent, Kandhasamy, Sarkunam, Montermini, Florian, Ollivier, Cyril, Panchaud, Philippe, Pozzi, Davide, Scanlan, Eoin Martin, Schaffner, Arnaud-Pierre, Weber, Valéry
Format: Article
Language:English
Subjects:
Alcohols
Alkenes
alkenylation
alkynylation
Allyl compounds
allylation
Boron
catecholboranes
Chains
Chemical reactions
cyanation
Derivatives
Hydroboration
hydrogen atom donor
Organic chemistry
organoboranes
Radicals
Reagents
reduction
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Summary:Boron derivatives are becoming key reagents in radical chemistry. Here, we describe reactions where an organoboron derivative is used as a radical initiator, a chain-transfer reagent, and a radical precursor. For instance, -alkylcatecholboranes, easily prepared by hydroboration of alkenes, represent a very efficient source of primary, secondary, and tertiary alkyl radicals. Their very high sensitivity toward oxygen- and heteroatom-centered radicals makes them particularly attractive for the development of radical chain processes such as conjugate addition, allylation, alkenylation, and alkynylation. Boron derivatives have also been used to develop an attractive new procedure for the reduction of radicals with alcohols and water. The selected examples presented here demonstrate that boron-containing reagents can efficiently replace tin derivatives in a wide range of radical reactions.
ISSN:0033-4545
1365-3075
DOI:10.1351/pac200779020223