Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

This chapter describes the use of allyl‐ and vinylstannane reagents for a variety of radical‐based transformations. The processes discussed include direct addition of radicals to allyl‐ and vinylstannanes, multicomponent or multistep cascade reactions that terminate with an intermolecular allylation or vinylation, cyclizations onto allyl‐ or vinylstannane moieties, and allylstannylation reactions. Allylation reactions have provided a framework for the exploration of stereoselective radical reactions, and models for explaining the stereoselectivity obtained by a number of approaches are presented. Examples are provided to illustrate the scope of applications of allyl‐ and vinylstannane radical reactions in synthesis, as well as the ways that the newly introduced allyl and vinyl groups have been subsequently manipulated. A comparison is made to radical allylation and vinylation reactions that employ non‐tin‐based reagents.