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. In this study we have discovered that trace molecular oxygen is necessary for any radical-mediated hydrostannylation to occur with a wide selection of alkynes with either B(Et)3 or AIBN leading us to propose a hybrid single-electron transfer (SET)/radical propagation mechanism. Additionally, B(C6F5)3 has also been shown to be a highly reactive and fully regio- and stereoselective catalyst for the hydrostannylation of propargylic alcohol derivatives, however it proceeds by a completely unique pathway. The mechanisms of these processes with be discussed in detail.

Recent advances in the hydrostannylation of propargylic alcohol derivatives

248th National Meeting (2014)

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