Preparation of 2,3-disubstituted indoles by sequential Larock heteroannulation and silicon-based cross-coupling reactions

Scott E. Denmark, John D. Baird

Research output: Contribution to journalArticle

Abstract

A simple and convergent synthesis of 2,3-disubstituted indoles has been developed using a sequential Larock indole synthesis and silicon-based, cross-coupling reaction. Substituted 2-iodoanilines reacted with an alkynyldimethylsilyl tert-butyl ether to afford indole-2-silanols under the Larock heteroannulation conditions after hydrolysis. The corresponding sodium 2-indolylsilanolate salts successfully engaged in cross-coupling with aryl bromides and chlorides to afford multi-substituted indoles. The development of an alkynyldimethylsilyl tert-butyl ether as a masked silanol equivalent enabled a smooth heteroannulation process and the identification of a suitable catalyst/ligand combination provided for a facile cross-coupling reaction.

Original languageEnglish (US)
Pages (from-to)3120-3129
Number of pages10
JournalTetrahedron
Volume65
Issue number16
DOIs
StatePublished - Apr 18 2009

Keywords

  • Alkynes
  • Cross-coupling
  • Indoles
  • Palladium catalysis
  • Silanols

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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