Facile solid-phase construction of indole derivatives based on a traceless, activating sulfonyl linker

[reaction: see text] Palladium-mediated coupling/intramolecular indole cyclization of terminal alkynes with resin 8, followed by cleavage of the sulfonamide linkage, were executed under mild conditions to provide diverse indoles 10 in excellent yield and purity. This chemistry benefits from a dual-activation process that derives from use of a traceless N-sulfonyl linker. Also, direct mercuration of 9 (X = H, R = 4-Me-C6H4), followed by palladium-mediated coupling with methyl acrylate, efficiently provided 3-functionalized product 12.