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

作者：Fukumoto Yoshiya^*; Daijo Masato; Chatani Naoto

来源：Journal of the American Chemical Society, 2012, 134(21): 8762-8765.

DOI：10.1021/ja3022818

The reaction of terminal allcynes 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 regio selective C-C bond forming reaction appears to involve the formation of an alkynyl rhenium species and subsequent nucleophilic attack of the alkynyl beta-carbon atom on the imine carbon to give a vinylidene rhenium species.

• 出版日期2012-5-30