Pd-Catalyzed Sequential C-N and C-C Coupling Route to 2-Vinylindoles

Significance

A one-pot Pd-catalyzed route to substituted 2-vinylindoles from readily accessible gem-dibromovinylanilines is reported. The reaction, involving a Buchwald-Hartwig amination/Heck sequence, proceeds in modest to good yields and appears not to be influenced greatly by substituent effects as seen from the thorough scope study. The intramolecular variant of this reaction to provide tricyclic pyrido- and azepino­indole derivatives is also described.