Issue 2, 2005

A comparative analysis of the functionalisation of unactivated cycloalkanes using alkynes and either sunlight or a photochemical reactor

Abstract

Using a standard mercury vapour lamp or sunlight, the synthetically difficult task of introducing functionality into unactivated cycloalkanes through C–C bond formation is accomplished in the presence of a soluble or supported photomediator and an alkyne bearing an electron-withdrawing group. The reaction involves the regiospecific addition of a photochemically generated cycloalkyl radical to the β-carbon of the alkyne. The use of solar radiation and a potentially recyclable polymer-bound photomediator for this fundamentally important synthetic process is particularly attractive from the clean/green chemistry perspective.

Graphical abstract: A comparative analysis of the functionalisation of unactivated cycloalkanes using alkynes and either sunlight or a photochemical reactor

Article information

Article type
Paper
Submitted
02 Aug 2004
Accepted
19 Oct 2004
First published
10 Dec 2004

Green Chem., 2005,7, 91-96

A comparative analysis of the functionalisation of unactivated cycloalkanes using alkynes and either sunlight or a photochemical reactor

R. A. Doohan and N. W. A. Geraghty, Green Chem., 2005, 7, 91 DOI: 10.1039/B411786G

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