Nickel-catalyzed addition of pyridine-N-oxides across alkynes

Kyalo Stephen Kanyiva; Yoshiaki Nakao; Tamejiro Hiyama

doi:10.1002/anie.200703758

Nickel-catalyzed addition of pyridine-N-oxides across alkynes

Kyalo Stephen Kanyiva^*, Yoshiaki Nakao, Tamejiro Hiyama

^*Corresponding author for this work

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

249 Citations (Scopus)

Abstract

(Chemical Equation Presented) An alternative to pyridine: Pyridine-N-oxides undergo direct C-H activation and add across alkynes under mild nickel catalysis to afford (E)-2-alkenylpyridine-N-oxides in modest to good yields with high selectivity. Subsequent deoxygenation and deoxygenative functionalization proceed smoothly to give a wide variety of 2-substituted pyridines. PCyp ₃ = tricyclopentylphosphine, cod = cyclooctadiene.

Original language	English
Pages (from-to)	8872-8874
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	46
DOIs	https://doi.org/10.1002/anie.200703758
Publication status	Published - 2007 Dec 10
Externally published	Yes

Keywords

Alkynes
C-C coupling
C-H activation
Nickel
Pyridine-N-oxides

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200703758

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title = "Nickel-catalyzed addition of pyridine-N-oxides across alkynes",

abstract = "(Chemical Equation Presented) An alternative to pyridine: Pyridine-N-oxides undergo direct C-H activation and add across alkynes under mild nickel catalysis to afford (E)-2-alkenylpyridine-N-oxides in modest to good yields with high selectivity. Subsequent deoxygenation and deoxygenative functionalization proceed smoothly to give a wide variety of 2-substituted pyridines. PCyp 3 = tricyclopentylphosphine, cod = cyclooctadiene.",

keywords = "Alkynes, C-C coupling, C-H activation, Nickel, Pyridine-N-oxides",

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

year = "2007",

month = dec,

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doi = "10.1002/anie.200703758",

language = "English",

volume = "46",

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AU - Kanyiva, Kyalo Stephen

AU - Nakao, Yoshiaki

AU - Hiyama, Tamejiro

PY - 2007/12/10

Y1 - 2007/12/10

N2 - (Chemical Equation Presented) An alternative to pyridine: Pyridine-N-oxides undergo direct C-H activation and add across alkynes under mild nickel catalysis to afford (E)-2-alkenylpyridine-N-oxides in modest to good yields with high selectivity. Subsequent deoxygenation and deoxygenative functionalization proceed smoothly to give a wide variety of 2-substituted pyridines. PCyp 3 = tricyclopentylphosphine, cod = cyclooctadiene.

AB - (Chemical Equation Presented) An alternative to pyridine: Pyridine-N-oxides undergo direct C-H activation and add across alkynes under mild nickel catalysis to afford (E)-2-alkenylpyridine-N-oxides in modest to good yields with high selectivity. Subsequent deoxygenation and deoxygenative functionalization proceed smoothly to give a wide variety of 2-substituted pyridines. PCyp 3 = tricyclopentylphosphine, cod = cyclooctadiene.

KW - Alkynes

KW - C-C coupling

KW - C-H activation

KW - Nickel

KW - Pyridine-N-oxides

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Nickel-catalyzed addition of pyridine-N-oxides across alkynes

Abstract

Keywords

ASJC Scopus subject areas

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