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The substitution of a functional group for a hydrogen atom is a very important transformation in synthetic organic chemistry. Reactions such as deoxygenations, deselenations, deaminations, dehalogenations, and decarboxylations fall into this category. Such reactions can be conducted efficiently using free radical chemistry. These defunctionalizations can be combined with C-C-bond forming processes. Radical reactions are generally conducted under very mild conditions. Various sensitive functional groups are tolerated under free radical conditions. Tin hydrides (Bu3SnH, Ph3SnH, Me3SnH) have been successfully employed in radical chemistry over the last 40 years, however there are drawbacks associated with tin-based chemistry. Organotin compounds are toxic and very often problems occur with product purification. Therefore, various attempts have been made to overcome these problems. In the present review article, we summarize the achievements on the development of tin hydride substitutes in reductive radical chain reactions.
Studer et al. (Tue,) studied this question.