Hydroheteroarylation of alkynes under mild nickel catalysis

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

Research output: Contribution to journalArticle

200 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
Externally publishedYes

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phosphine
Alkynes
Nickel
Catalysis
Ligands
Regioselectivity
Chemical activation
ethylene
3-cyanoindole

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Hydroheteroarylation of alkynes under mild nickel catalysis. / Nakao, Yoshiaki; Kanyiva, Stephen Kyalo; Oda, Shinichi; Hiyama, Tamejiro.

In: Journal of the American Chemical Society, Vol. 128, No. 25, 28.06.2006, p. 8146-8147.

Research output: Contribution to journalArticle

Nakao, Yoshiaki ; Kanyiva, Stephen Kyalo ; Oda, Shinichi ; Hiyama, Tamejiro. / Hydroheteroarylation of alkynes under mild nickel catalysis. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 25. pp. 8146-8147.
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