Synthesis of 2,3-Disubstituted Indoles by Palladium-Mediated Coupling of 2-Iodoindoles

All articles of this category N -Unprotected 2-iodoindoles are synthesized by treatment of 2-stannylindoles with iodine, which in turn are prepared by tin-mediated radical cyclization of 2-alkenylphenylisocyanides. Palladium-catalyzed coupling reactions of N -unprotected 2-iodoindoles with terminal acetylenes, terminal olefins, carbonylation, and the Suzuki coupling reaction with phenyl borate proceed smoothly to furnish the corresponding 2,3-disubstituted indoles in good to excellent yields. 2-iodoindole - 2-stannylindole - isonitrile - radical cyclization - palladium-mediated coupling