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Chemoselective Amination of Propargylic C(sp 3 )H Bonds by Cobalt(II)‐Based Metalloradical Catalysis
Author(s) -
Lu Hongjian,
Li Chaoqun,
Jiang Huiling,
Lizardi Christopher L.,
Zhang X. Peter
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.201400557
Subject(s) - amination , cobalt , catalysis , chemistry , bond , medicinal chemistry , combinatorial chemistry , organic chemistry , business , finance
Abstract Highly chemoselective intramolecular amination of propargylic C(sp 3 )H bonds has been demonstrated for N‐bishomopropargylic sulfamoyl azides through cobalt(II)‐based metalloradical catalysis. Supported by D 2h ‐symmetric amidoporphyrin ligand 3,5‐Di t Bu‐IbuPhyrin, the cobalt(II)‐catalyzed CH amination proceeds effectively under neutral and nonoxidative conditions without the need of any additives, and generates N 2 as the only byproduct. The metalloradical amination is suitable for both secondary and tertiary propargylic CH substrates with an unusually high degree of functional‐group tolerance, thus providing a direct method for high‐yielding synthesis of functionalized propargylamine derivatives.