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 h eteroannulation of 1-alkyl-2-(trimethyl- silyl)acetylene with amide resin-b ound o-iodoaniline 1. followed by transformation of trimethylsilyl to iodid e and then Suzuki coupling reactions. Traceless synthesis of symmetrical an d unsymmetrical 2,3-diarylindoles was achieved via palladium-mediated one-p ot coupling/intramolecular indole cyclization of aryl-subslituted terminal alkynes with sulfonyl resin-bound o-iodoaniline 6, followed by regioselecti ve bromination and Suzuki coupling reactions. (C) 2001 Elsevier Science Ltd . All rights reserved.