2,2'-Azobis (2-methylpropionitrile) -mediated alkyne hydrostannylation: reaction mechanism
Oderinde, M.S.; Froese, R.D.J.; Organ, M.G.
Angewandte Chemie 52(43): 11334-11338
Not as radical as you think: The free-radical hydrostannylation of alkynes has been extensively studied and while every published mechanism involves solely radical intermediates, this appears not to be correct. Trace molecular oxygen is necessary for any radical-mediated hydrostannylation to occur with a wide selection of alkynes, thus leading to a proposed hybrid single-electron transfer/radical propagation mechanism. AIBN=2,2'-azobis(2-methylpropionitrile).