An Efficient and Practical Tin Free Procedure for Radical Iodine Atom-Transfer Reactions

Cyril Ollivier; Thomas Bark; Philippe Renaud

doi:10.1055/s-2000-7603

Synthesis 2000; 2000(11): 1598-1602
DOI: 10.1055/s-2000-7603

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An Efficient and Practical Tin Free Procedure for Radical Iodine Atom-Transfer Reactions

Cyril Ollivier^* , Thomas Bark, Philippe Renaud

^*Université de Fribourg, Institut de Chimie Organique, Pérolles, CH-1700 Fribourg, Switzerland; Fax + 41 (0) 2 63 00 96 55; E-mail: philippe.renaud@unifr.ch

Abstract

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Iodine atom-transfer is a non-reductive and very attractive way of performing radical reactions that is usually achieved in the presence of hexaalkyldistannanes. We report here an efficient procedure to run such reactions in the absence of ditin derivatives. The iodine atom transfers are performed via thermal initiation with commercially available and cheap dilauroyl peroxide (DLP). Good yields for intra- and intermolecular addition to alkenes are obtained. One example of aromatic substitution for the synthesis of an indolone derivative using stoichiometric amount of DLP is also reported.

radical reactions - iodine - peroxides - isomerization - ring closure

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