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Studies on the Mechanism of B(C 6 F 5 ) 3 ‐Catalyzed Hydrostannylation of Propargylic Alcohol Derivatives
Author(s) -
Oderinde Martins S.,
Organ Michael G.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204060
Subject(s) - stannane , hydride , chemistry , stereoselectivity , deuterium , borohydride , stereochemistry , medicinal chemistry , catalysis , combinatorial chemistry , organic chemistry , physics , hydrogen , nuclear physics
Sleight of hydride : B(C 6 F 5 ) 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.