Synthesis of allylamides from allyl halides, carbon monoxide, and titanium–nitrogen complexes prepared from molecular nitrogen

Abstract

4-Phenylbut-3-enamide could be synthesized from corresponding 3-chloroprop-2-enylbenzene, carbon monoxide (1 atm), and titanium–nitrogen complexes, prepared from Ti(O i Pr) 4, Li, TMSCl, and molecular nitrogen (1 atm), using a palladium catalyst. The reaction proceeds via transmetalation of the titanium–nitrogen complex to an acylpalladium complex. P t Bu 3 as a ligand of the palladium catalyst, afforded a good result, and the amounts of Li and TMSCl affected the yield of amide. When the reaction was carried out using a bidentate ligand on the palladium complex under an atmosphere of argon instead of carbon monoxide, an allylamine derivative was obtained.