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)