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

摘要

Radical reactions using tribenzyltin hydride (Bn_3SnH) easily prepared from tin and benzyl chloride were studied. The Et_3B- initiated reduction and cyclization of haloalkanes and haloalkenes with Bn _3SnH proceeded efficiently. Homolytic hydrostannylation of alkynes with Bn_3SnH 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 (Bn _3SnCl) easily decomposed to benzyl alcohol in a basic solution of H_2O_2.