Monoallylstannanes, reagents for allylic radical transfer. Part I

Abstract

We have previously highlighted the ability of the N,N-bistrimethylsilylaminostannylene 1 to produce monoallylstannanes 2 in quantitative yields, starting from various functionalised allylic halides via an insertion reaction. In contrast with more electrophilic trihalogenotin radicals, the tin-centred radicals generated from reagents 2 are shown to be the best candidates towards allylic radical transfer, giving allylated products in similar yields as those obtained with classical tributyltin radicals.