B(C6F5)3 has been shown to be a highly reactive and fully regio- and stereoselective catalyst for the hydrostannylation of propargylic alcohol derivatives. This Lewis acid first abstracts a hydride from the stannane forming a borohydride/stannyl cation pair, which shows solvent/ligand dependency. Unexpectedly, deuterium labeling has demonstrated that the borohydride is not the ultimate hydride donor, rather a second molecule of stannane reduces the alkenyl cation intermediate.

Studies on the mechanism of B(C6F5)3-catalyzed hydrostannylation of propargylic alcohol derivatives

247th National Meeting (2014)

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