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

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130 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 languageEnglish
Pages (from-to)6098-6099
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number19
DOIs
Publication statusPublished - 2007 May 16

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Ruthenium
Aniline
Aniline Compounds
Nitrogen
Carbon
Derivatives
Toluene
Carbon Monoxide
Esters
Acids
aniline
benzeneboronic acid
2,2-dimethyl-1,3-propanediol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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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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T1 - Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates

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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