Palladium-catalyzed carbene insertion into vinyl halides and trapping with amines.
Palladium is shown to catalyze the three-component coupling of vinyl halides, trimethylsilyldiazomethane, and amines to generate allylamines. The mechanism is believed to involve formation of an R-Pd=CHSiMe3 intermediate that undergoes migration of the vinyl ligand to the empty p-orbital of the carbene ligand. The resulting eta1-allylpalladium species forms an eta3-allylpalladium intermediate that is trapped by the amine nucleophile. Under the conditions tested, cyclic secondary amines and terminal vinyl iodides give the best results.
Devine
Sean K J
SK
Department of Chemistry, 1102 Natural Sciences, University of California, Irvine, CA 92697-2025, USA.
Van  Vranken
David L
DL