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Thiyl radicals in organic synthesis

Type of publication Peer-reviewed
Publikationsform Review article (peer-reviewed)
Publication date 2014
Author Dénès Fabrice, Pichowicz Mark, Povie Guillaume, Renaud Philippe,
Project Synthetic Methods for total Synthesis of Natural Products
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Review article (peer-reviewed)

Journal Chemical Reviews
Volume (Issue) 114(5)
Page(s) 2587 - 2693
Title of proceedings Chemical Reviews
DOI 10.1021/cr400441m

Abstract

The review covers the uses of thiyl radicals in organic synthesis and provides mechanistic information to understand these processes and to design new synthetic applications. It describes the main elementary reactions involving thiyl radicals and discusses the factors directing the rates and selectivity of these processes. The reaction of sulfur-containing molecules with another radical is a preeminent source of thiyl radicals. Thiols can rapidly transfer a hydrogen atom to most types of radical X having a corresponding higher X-H BDE. All the commonly used initiators such as azo-compounds or peroxides that generate alkyl or alkoxyl radicals are efficient to initiate thiol-mediated radical transformations.
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