Synthetic utility of tribenzyltin hydride and its derivatives as easily accessible, removable, and decomposable organotin reagents

Radical reactions using tribenzyltin hydride (Bn3SnH) easily prepared from tin and benzyl chloride were studied. The Et3B-initiated reduction and cyclization of haloalkanes and haloalkenes with Bn3SnH proceeded efficiently. Homolytic hydrostannylation of alkynes with Bn3SnH followed by treatment with electrophiles gave functionalized alkenes in good to high yields. The organotin byproducts formed could be easily removable by filtration and silica-gel column chromatography without any pretreatment. It was also found that tribenzyltin chloride (Bn3SnCl) easily decomposed to benzyl alcohol in a basic solution of H2O2.