Rhodium-catalyzed C-H-CO-olefin coupling reactions - A chelation-assisted direct carbonylation at the ortho C-H bond in the benzene ring of 2-arylpyridines

Naoto Chatani; Takeshi Uemura; Taku Asaumi; Yutaka Ie; Fumitoshi Kakiuchi; Shinji Murai

doi:10.1139/v05-077

Rhodium-catalyzed C-H-CO-olefin coupling reactions - A chelation-assisted direct carbonylation at the ortho C-H bond in the benzene ring of 2-arylpyridines

Naoto Chatani, Takeshi Uemura, Taku Asaumi, Yutaka Ie, Fumitoshi Kakiuchi, Shinji Murai

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

28 Citations (Scopus)

Abstract

The reaction of 2-arylpyridines with ethylene and carbon monoxide in the presence of a catalytic amount of Rh₄(CO)₁₂ results in selective carbonylation at the ortho C-H bond. The reaction is heavily dependent on the solvents used, with DMA (N,N-dimethylacetamide) being the solvent of choice. Steric factors are also important determinants of the efficiency of the reaction.

Original language	English
Pages (from-to)	755-763
Number of pages	9
Journal	Canadian Journal of Chemistry
Volume	83
Issue number	6-7
DOIs	https://doi.org/10.1139/v05-077
Publication status	Published - 2005 Jun 1
Externally published	Yes

Keywords

C-H bond activation
Carbon monoxide
Carbonylation
Chelation
Rhodium

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Organic Chemistry

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title = "Rhodium-catalyzed C-H-CO-olefin coupling reactions - A chelation-assisted direct carbonylation at the ortho C-H bond in the benzene ring of 2-arylpyridines",

abstract = "The reaction of 2-arylpyridines with ethylene and carbon monoxide in the presence of a catalytic amount of Rh4(CO)12 results in selective carbonylation at the ortho C-H bond. The reaction is heavily dependent on the solvents used, with DMA (N,N-dimethylacetamide) being the solvent of choice. Steric factors are also important determinants of the efficiency of the reaction.",

keywords = "C-H bond activation, Carbon monoxide, Carbonylation, Chelation, Rhodium",

author = "Naoto Chatani and Takeshi Uemura and Taku Asaumi and Yutaka Ie and Fumitoshi Kakiuchi and Shinji Murai",

year = "2005",

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doi = "10.1139/v05-077",

language = "English",

volume = "83",

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T1 - Rhodium-catalyzed C-H-CO-olefin coupling reactions - A chelation-assisted direct carbonylation at the ortho C-H bond in the benzene ring of 2-arylpyridines

AU - Chatani, Naoto

AU - Uemura, Takeshi

AU - Asaumi, Taku

AU - Ie, Yutaka

AU - Kakiuchi, Fumitoshi

AU - Murai, Shinji

PY - 2005/6/1

Y1 - 2005/6/1

N2 - The reaction of 2-arylpyridines with ethylene and carbon monoxide in the presence of a catalytic amount of Rh4(CO)12 results in selective carbonylation at the ortho C-H bond. The reaction is heavily dependent on the solvents used, with DMA (N,N-dimethylacetamide) being the solvent of choice. Steric factors are also important determinants of the efficiency of the reaction.

AB - The reaction of 2-arylpyridines with ethylene and carbon monoxide in the presence of a catalytic amount of Rh4(CO)12 results in selective carbonylation at the ortho C-H bond. The reaction is heavily dependent on the solvents used, with DMA (N,N-dimethylacetamide) being the solvent of choice. Steric factors are also important determinants of the efficiency of the reaction.

KW - C-H bond activation

KW - Carbon monoxide

KW - Carbonylation

KW - Chelation

KW - Rhodium

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EP - 763

JO - Canadian Journal of Chemistry

JF - Canadian Journal of Chemistry

IS - 6-7

ER -

Rhodium-catalyzed C-H-CO-olefin coupling reactions - A chelation-assisted direct carbonylation at the ortho C-H bond in the benzene ring of 2-arylpyridines

Abstract

Keywords

ASJC Scopus subject areas

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