1126650-52-9Relevant academic research and scientific papers
Rhenium-catalyzed regio- and stereoselective addition of imines to terminal alkynes leading to n -alkylideneallylamines
Fukumoto, Yoshiya,Daijo, Masato,Chatani, Naoto
supporting information; experimental part, p. 8762 - 8765 (2012/07/02)
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.
