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 Vol. 79; no. 2; pp. 223 - 233 |
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Main Authors | , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Berlin
De Gruyter
01.02.2007
Walter de Gruyter GmbH |
Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 0033-4545 1365-3075 |
DOI: | 10.1351/pac200779020223 |