Construction of Indole and Benzofuran Systems on the Solid Phase via Palladium-Mediated Cyclizations1

Molecular diversity in the area of nonpeptide, small organic molecules has been receiving considerable attention in the chemical community. Herein, we report new solid-phase methodology for the rapid generation of such small-molecule libraries by simultaneous-parallel or combinatorial synthesis. We have adapted a palladium-mediated, intramolecular Heck-type reaction, a mild and versatile method for carbon−carbon bond formation, to the solid phase. This has been applied to the synthesis of diverse indole and benzofuran derivatives, such as 8, 15, and 28, in good to excellent yields.