Palladium-catalyzed annulation of haloanilines and halobenzamides using norbornadiene as an acetylene synthon: a route to functionalized indolines, isoquinolinones, and indoles.

A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.