Hydroheteroarylation of alkynes under mild nickel catalysis

Yoshiaki Nakao, Kyalo Stephen Kanyiva, Shinichi Oda, Tamejiro Hiyama

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204 Citations (Scopus)

Abstract

Nickel complexes having a bulky tri(sec-alkyl)phosphine ligand catalyze hydroheteroarylation of alkynes at 35 °C. Selective activation of an Ar-H bond over an Ar-CN bond of N-protected 3-cyanoindoles is achieved by a proper choice of ligand and/or an N-protecting group. The catalysis is applicable to a diverse range of heteroarenes to afford cis-hydroheteroarylation products in highly chemo- and stereoselective manners. Excellent regioselectivity is observed with unsymmetrical alkynes to give the corresponding heteroaryl-substituted ethenes having a larger substituent trans to an aryl group.

Original languageEnglish
Pages (from-to)8146-8147
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number25
DOIs
Publication statusPublished - 2006 Jun 28

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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