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Studies on the Mechanism of B(C6F5)3-Catalyzed Hydrostannylation of Propargylic Alcohol Derivatives

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  • This work was supported by NSERC (Canada) and The Ontario Research Fund (ORF) (Ontario).

Abstract

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Sleight of hydride: B(C6F5)3 catalyzes the hydrostannylation of propargylic alcohols in a regio- and stereoselective manner (see scheme). This Lewis acid first abstracts a hydride from the stannane, thus forming a borohydride/stannyl cation pair, the stability of which depends on solvent and ligands. Deuterium-labeling experiments showed that the source that delivers a hydride to the alkenyl cation is not the borohydride but rather a second molecule of stannane.

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