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Title: Metal-free σ-bond metathesis in 1,3,2-diazaphospholene-catalyzed hydroboration of carbonyl compounds
Authors: Chong, Che Chang
Hirao, Hajime
Kinjo, Rei
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Carbanions
Issue Date: 2015
Source: Chong, C. C., Hirao, H., & Kinjo, R. (2015). Metal-free σ-bond metathesis in 1,3,2-diazaphospholene-catalyzed hydroboration of carbonyl compounds. Angewandte chemie international edition, 54(1), 190-194.
Series/Report no.: Angewandte chemie international edition
Abstract: The first metal-free catalytic hydroboration of carbonyl derivatives has been developed in which a catalytic amount of 1,3,2-diazaphospholene effectively promotes a hydroboration reaction of aliphatic and aromatic aldehydes and ketones. The reaction mechanism involves the cleavage of both the P-O bond of the alkoxyphosphine intermediate and the B-H bond of pinacolborane as well as the formation of P-H and B-O bonds. Thus, the reaction proceeds through a non-metal σ-bond metathesis. Kinetic and computational studies suggest that the σ-bond metathesis occurred in a stepwise but nearly concerted manner.
ISSN: 1433-7851
DOI: 10.1002/anie.201408760
Rights: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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