A variety of 3-substituted β- and γ-carbolines have been synthesized from N-substituted 3-iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, respectively. The coupling of thesealdehydes with various terminal acetylenes with PdCl2(PPh3)2/CuI as the catalyst readily affordsthe corresponding alkynylindole carboxaldehydes, which have subsequently been converted to thecorresponding tert-butylimines and cyclized to β- and γ-carbolines by either copper-catalyzed orthermal processes.