Efficient synthesis of 3-substituted 2-arylindoles via Suzuki coupling reactions on the solid phase

2-Aryl-3-alkylindoles were prepared on solid phase via palladium-mediated heteroannulation of 1-alkyl-2-(trimethylsilyl)acetylene with amide resin-bound o-iodoaniline 1, followed by transformation of trimethylsilyl to iodide and then Suzuki coupling reactions. Traceless synthesis of symmetrical and unsymmetrical 2,3-diarylindoles was achieved via palladium-mediated one-pot coupling/intramolecular indole cyclization of aryl-substituted terminal alkynes with sulfonyl resin-bound o-iodoaniline 6, followed by regioselective bromination and Suzuki coupling reactions.