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A Concerted Transfer Hydrogenolysis: 1,3,2‐Diazaphospholene‐Catalyzed Hydrogenation of NN Bond with Ammonia–Borane
Author(s) -
Chong Che Chang,
Hirao Hajime,
Kinjo Rei
Publication year - 2014
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.201400099
Subject(s) - hydrogenolysis , ammonia borane , chemistry , catalysis , borane , hydrazine (antidepressant) , transfer hydrogenation , ammonia , photochemistry , medicinal chemistry , double bond , organic chemistry , ruthenium , hydrogen production , chromatography
1,3,2‐diazaphospholenes catalyze metal‐free transfer hydrogenation of a NN double bond using ammonia–borane under mild reaction conditions, thus allowing access to various hydrazine derivatives. Kinetic and computational studies revealed that the rate‐determining step involves simultaneous breakage of the BH and NH bonds of ammonia–borane. The reaction is therefore viewed as a concerted type of hydrogenolysis.