On the Scope of Radical Reactions Utilizing InCl3/coreductant as an Efficient Reagent for Synthetically Useful Transformations in Aqueous and Organic Solvents

A broad range of free radical transformations such as hydrogen atom transfer, halogen atom transfer, radical cascade, deoxygenations, and additions to olefins and alkynes have been investigated in the presence of InCl3/coreductant (Bu3SnH, TMS3SiH, H3PO2 or NaBH4) as an efficient hydrogen donor system in water. Reactions proceeded smoothly and in excellent yields, with InCl3 playing a dual role as efficient initiator and hydrogen donor. The approach has expanded the kinetic range, stereospecificity as well as broadened the applicability of the free radical transformations in aqueous media. Mechanistic aspects of described transformations are also addressed.