Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines. Direct carbonylation at a C-H bond δ to the pyridine nitrogen

Naoto Chatani; Shuhei Yorimitsu; Taku Asaumi; Fumitoshi Kakiuchi; Shinji Murai

doi:10.1021/jo0259865

Ru₃(CO)₁₂-catalyzed C-H/CO/olefin coupling of N-pyridylindolines. Direct carbonylation at a C-H bond δ to the pyridine nitrogen

Naoto Chatani, Shuhei Yorimitsu, Taku Asaumi, Fumitoshi Kakiuchi, Shinji Murai

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

70 Citations (Scopus)

Abstract

The reaction of N-pyridylindolines with CO and ethylene in the presence of Ru₃(CO)₁₂ results in direct carbonylation at a C-H bond δ to the pyridine Sp² nitrogen, which represents a new type of C-H/CO/olefin coupling. The presence of a pyridine ring as a directing group on the substrates is essential for the reaction to proceed. The choice of N,N-dimethylacetamide (DMA) as the solvent is crucial for the reaction to proceed efficiently.

Original language	English
Pages (from-to)	7557-7560
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	67
Issue number	21
DOIs	https://doi.org/10.1021/jo0259865
Publication status	Published - 2002 Oct 18
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The reaction of N-pyridylindolines with CO and ethylene in the presence of Ru3(CO)12 results in direct carbonylation at a C-H bond δ to the pyridine Sp2 nitrogen, which represents a new type of C-H/CO/olefin coupling. The presence of a pyridine ring as a directing group on the substrates is essential for the reaction to proceed. The choice of N,N-dimethylacetamide (DMA) as the solvent is crucial for the reaction to proceed efficiently.",

author = "Naoto Chatani and Shuhei Yorimitsu and Taku Asaumi and Fumitoshi Kakiuchi and Shinji Murai",

year = "2002",

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T1 - Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines. Direct carbonylation at a C-H bond δ to the pyridine nitrogen

AU - Chatani, Naoto

AU - Yorimitsu, Shuhei

AU - Asaumi, Taku

AU - Kakiuchi, Fumitoshi

AU - Murai, Shinji

PY - 2002/10/18

Y1 - 2002/10/18

N2 - The reaction of N-pyridylindolines with CO and ethylene in the presence of Ru3(CO)12 results in direct carbonylation at a C-H bond δ to the pyridine Sp2 nitrogen, which represents a new type of C-H/CO/olefin coupling. The presence of a pyridine ring as a directing group on the substrates is essential for the reaction to proceed. The choice of N,N-dimethylacetamide (DMA) as the solvent is crucial for the reaction to proceed efficiently.

AB - The reaction of N-pyridylindolines with CO and ethylene in the presence of Ru3(CO)12 results in direct carbonylation at a C-H bond δ to the pyridine Sp2 nitrogen, which represents a new type of C-H/CO/olefin coupling. The presence of a pyridine ring as a directing group on the substrates is essential for the reaction to proceed. The choice of N,N-dimethylacetamide (DMA) as the solvent is crucial for the reaction to proceed efficiently.

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JF - Journal of Organic Chemistry

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ER -

Ru₃(CO)₁₂-catalyzed C-H/CO/olefin coupling of N-pyridylindolines. Direct carbonylation at a C-H bond δ to the pyridine nitrogen

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