Studies on the Mechanism of B(C 6 F 5 ) 3 ‐Catalyzed Hydrostannylation of Propargylic Alcohol Derivatives | Zendy

Oderinde Martins S. | Zendy; Organ Michael G. | Zendy

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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.

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