Rhenium-Catalyzed Regio- and Stereoselective Addition of Imines to Terminal Alkynes Leading to N-Alkylideneallylamines

The reaction of terminal alkynes with imines using ReBr(CO)5 as a catalyst results in the production of N-alkylideneallylamines and not the conventional propargylamines. The substituent on the imine nitrogen is important, and a diphenylmethyl group gave the best result. The catalytic cycle of this r...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2012-05, Vol.134 (21), p.8762-8765
Main Authors: Fukumoto, Yoshiya, Daijo, Masato, Chatani, Naoto
Format: Article
Language:English
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Summary:The reaction of terminal alkynes with imines using ReBr(CO)5 as a catalyst results in the production of N-alkylideneallylamines and not the conventional propargylamines. The substituent on the imine nitrogen is important, and a diphenylmethyl group gave the best result. The catalytic cycle of this regioselective C–C bond forming reaction appears to involve the formation of an alkynyl rhenium species and subsequent nucleophilic attack of the alkynyl β-carbon atom on the imine carbon to give a vinylidene rhenium species.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3022818