Rhenium-catalyzed regio- and stereoselective addition of imines to terminal alkynes leading to N-alkylideneallylamines.

@article{Fukumoto2012RheniumcatalyzedRA,
  title={Rhenium-catalyzed regio- and stereoselective addition of imines to terminal alkynes leading to N-alkylideneallylamines.},
  author={Yoshiya Fukumoto and Masato Daijo and Naoto Chatani},
  journal={Journal of the American Chemical Society},
  year={2012},
  volume={134 21},
  pages={8762-5}
}
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… CONTINUE READING