Synthesis of indoles via palladium-catalyzed annulation of aryl chlorides and internal alkynes

Thesis (S.M.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2005.Includes bibliographical references (leaves 34-35).A palladium-catalyzed preparation of 2,3-disubstituted indoles from commercially available and relatively inexpensive reagents, o-chloroacetanilide and internal alkynes, is reported. The system is efficient in delivering 2,3-disubstituted indoles in good to excellent yield with a high level of regioselectivity in most cases. Alkynes with alkyl, aryl, alkenyl, and trialkylsilyl substituents are compatible with this methodology.by Daemian David Dussault.S.M