CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2007, Vol. 79, No. 2, pp. 223-233

Boron: A key element in radical reactions

Philippe Renaud, Alice Beauseigneur, Andrea Brecht-Forster, Barbara Becattini, Vincent Darmency, Sarkunam Kandhasamy, Florian Montermini, Cyril Ollivier, Philippe Panchaud, Davide Pozzi, Eoin Martin Scanlan, Arnaud-Pierre Schaffner and Valéry Weber

Department of Chemistry and Biochemistry, University of Berne, Freiestrasse 3, CH-3000 Berne 9, Switzerland

Abstract: 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, B-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.