Cleavage of C-N bonds in aniline derivatives on a ruthenium center and its relevance to catalytic C-C bond formation

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Abstract

(Chemical Equation Presented) The first observation of cleavage of unactivated aromatic C-N bonds on a late-transitionmetal center was achieved using o-acylanilines and a ruthenium complex. Use of olefins as additives dramatically improved the rate of C?N bond cleavage. The carbon fragment remaining on the ruthenium after C?N bond cleavage was coupled with a phenylboronate to form a biphenyl framework. The present results suggest that ruthenium-catalyzed C-C bond formation from o-acylaniline and organoboronate proceeds via direct C?N bond cleavage on the ruthenium center.

Original languageEnglish
Pages (from-to)7238-7239
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number21
DOIs
Publication statusPublished - 2009 Jun 3

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Ruthenium
Aniline
Derivatives
Alkenes
Olefins
Carbon
Observation
aniline

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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title = "Cleavage of C-N bonds in aniline derivatives on a ruthenium center and its relevance to catalytic C-C bond formation",
abstract = "(Chemical Equation Presented) The first observation of cleavage of unactivated aromatic C-N bonds on a late-transitionmetal center was achieved using o-acylanilines and a ruthenium complex. Use of olefins as additives dramatically improved the rate of C?N bond cleavage. The carbon fragment remaining on the ruthenium after C?N bond cleavage was coupled with a phenylboronate to form a biphenyl framework. The present results suggest that ruthenium-catalyzed C-C bond formation from o-acylaniline and organoboronate proceeds via direct C?N bond cleavage on the ruthenium center.",
author = "Tetsuro Koreeda and Takuya Kochi and Fumitoshi Kakiuchi",
year = "2009",
month = "6",
day = "3",
doi = "10.1021/ja902829p",
language = "English",
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journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
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T1 - Cleavage of C-N bonds in aniline derivatives on a ruthenium center and its relevance to catalytic C-C bond formation

AU - Koreeda, Tetsuro

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

PY - 2009/6/3

Y1 - 2009/6/3

N2 - (Chemical Equation Presented) The first observation of cleavage of unactivated aromatic C-N bonds on a late-transitionmetal center was achieved using o-acylanilines and a ruthenium complex. Use of olefins as additives dramatically improved the rate of C?N bond cleavage. The carbon fragment remaining on the ruthenium after C?N bond cleavage was coupled with a phenylboronate to form a biphenyl framework. The present results suggest that ruthenium-catalyzed C-C bond formation from o-acylaniline and organoboronate proceeds via direct C?N bond cleavage on the ruthenium center.

AB - (Chemical Equation Presented) The first observation of cleavage of unactivated aromatic C-N bonds on a late-transitionmetal center was achieved using o-acylanilines and a ruthenium complex. Use of olefins as additives dramatically improved the rate of C?N bond cleavage. The carbon fragment remaining on the ruthenium after C?N bond cleavage was coupled with a phenylboronate to form a biphenyl framework. The present results suggest that ruthenium-catalyzed C-C bond formation from o-acylaniline and organoboronate proceeds via direct C?N bond cleavage on the ruthenium center.

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