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Keywords:

  • alkenylation;
  • amination;
  • C[BOND]H activation;
  • cyclization;
  • palladium;
  • phenanthridines

Abstract

A new protocol for the palladium-catalyzed free-amine-directed alkenylation of C(sp2)[BOND]H bonds and cycloamination is described. Substituted biaryl-2-amines react with various alkenes, including electron-deficient alkenes, aryl alkenes and alkyl alkenes, to give the corresponding phenanthridines with exclusive regioselectivity. The use of α-branched styrenes leads to the formation of tricyclic compounds with a seven-membered amine ring. The method operates through a free-amine-directed alkenylation and a subsequent hydroamination cyclization reaction.