Hydroheteroarylation of alkynes under mild nickel catalysis

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

doi:10.1021/ja0623459

Hydroheteroarylation of alkynes under mild nickel catalysis

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

234 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 language	English
Pages (from-to)	8146-8147
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	25
DOIs	https://doi.org/10.1021/ja0623459
Publication status	Published - 2006 Jun 28
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Hydroheteroarylation of alkynes under mild nickel catalysis",

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.",

author = "Yoshiaki Nakao and Kanyiva, {Kyalo Stephen} and Shinichi Oda and Tamejiro Hiyama",

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AU - Nakao, Yoshiaki

AU - Kanyiva, Kyalo Stephen

AU - Oda, Shinichi

AU - Hiyama, Tamejiro

PY - 2006/6/28

Y1 - 2006/6/28

N2 - 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.

AB - 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.

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JF - Journal of the American Chemical Society

IS - 25

ER -

Hydroheteroarylation of alkynes under mild nickel catalysis

Abstract

ASJC Scopus subject areas

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