“…The palladium-catalyzed coupling reactions of o -haloaniline derivatives offer valuable alternatives to the Fischer indole synthesis. , As part of the projected total syntheses of structurally complex indole alkaloids, a flexible method for installing an indole scaffold to an advanced intermediate at a late stage of synthesis was required; and a new approach of employing ketones or aldehydes that are regioisomeric to the substrates for the Fischer indole synthesis and variants was highly desirable. , An operationally expedient method for preparing N –H indoles without the use of an N -protecting group, while accessing all substitution patterns was also ideal. Toward this end, an effective strategy was recently found in oxidative cyclization of 2-alkenylanilines, which were easily accessible from o -haloanilines. We report herein a convenient synthesis of indoles by the sequential implementation of Pd-catalyzed cross-coupling reactions of o -haloanilines and oxidative cyclization of the resulting 2-alkenylanilines (Scheme ).…”