Domino or Single-Step Tsuji–Trost/Heck Reactions and Their Application in the Synthesis of 3-Benzazepines and Azepino[4,5-b]indole Ring Systems



A series of methods for palladium-mediated single-step and domino Tsuji–Trost/Heck reactions are described. These methods are applied to the synthesis of both 3-benzazepines and azepino[4,5-b]indoles in the category of complex 6-7-6 and 6-5-7 ring heterocycles. In addition, a domino Heck/Heck sequence of reactions that produces the azepinobenzindolizine tetracyclic ring system from N-diallylated precursors is described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)