Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates

Satoshi Ueno; Naoto Chatani; Fumitoshi Kakiuchi

doi:10.1021/ja0713431

Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates

Satoshi Ueno, Naoto Chatani, Fumitoshi Kakiuchi

Department of Chemistry

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

169 Citations (Scopus)

Abstract

The RuH₂(CO)(PPh₃)₃-catalyzed reaction of 2-amino-6-methylacetophenone with phenylboronic acid 2,2-dimethyl-1,3-propanediol ester in refluxing toluene gave the corresponding phenylation product in 83% yield via aryl carbon-nitrogen bond cleavage. This reaction involves two notable features: (1) the coupling proceeds via the oxidative addition of an aryl carbon-nitrogen bond in anilines to the ruthenium complex, and (2) C-C bond formation takes place via transmetalation between the Ru-NR₂ species and organoboronates.

Original language	English
Pages (from-to)	6098-6099
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	19
DOIs	https://doi.org/10.1021/ja0713431
Publication status	Published - 2007 May 16

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates",

abstract = "The RuH2(CO)(PPh3)3-catalyzed reaction of 2-amino-6-methylacetophenone with phenylboronic acid 2,2-dimethyl-1,3-propanediol ester in refluxing toluene gave the corresponding phenylation product in 83% yield via aryl carbon-nitrogen bond cleavage. This reaction involves two notable features: (1) the coupling proceeds via the oxidative addition of an aryl carbon-nitrogen bond in anilines to the ruthenium complex, and (2) C-C bond formation takes place via transmetalation between the Ru-NR2 species and organoboronates.",

author = "Satoshi Ueno and Naoto Chatani and Fumitoshi Kakiuchi",

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doi = "10.1021/ja0713431",

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AU - Ueno, Satoshi

AU - Chatani, Naoto

AU - Kakiuchi, Fumitoshi

PY - 2007/5/16

Y1 - 2007/5/16

N2 - The RuH2(CO)(PPh3)3-catalyzed reaction of 2-amino-6-methylacetophenone with phenylboronic acid 2,2-dimethyl-1,3-propanediol ester in refluxing toluene gave the corresponding phenylation product in 83% yield via aryl carbon-nitrogen bond cleavage. This reaction involves two notable features: (1) the coupling proceeds via the oxidative addition of an aryl carbon-nitrogen bond in anilines to the ruthenium complex, and (2) C-C bond formation takes place via transmetalation between the Ru-NR2 species and organoboronates.

AB - The RuH2(CO)(PPh3)3-catalyzed reaction of 2-amino-6-methylacetophenone with phenylboronic acid 2,2-dimethyl-1,3-propanediol ester in refluxing toluene gave the corresponding phenylation product in 83% yield via aryl carbon-nitrogen bond cleavage. This reaction involves two notable features: (1) the coupling proceeds via the oxidative addition of an aryl carbon-nitrogen bond in anilines to the ruthenium complex, and (2) C-C bond formation takes place via transmetalation between the Ru-NR2 species and organoboronates.

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Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates

Abstract

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