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

✍ Scribed by Han-Cheng Zhang; Hong Ye; Kimberly B White; Bruce E Maryanoff

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 96 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00857-7

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✦ Synopsis

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.

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