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

Tetsuro Koreeda; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1021/ja902829p

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

Tetsuro Koreeda, Takuya Kochi, Fumitoshi Kakiuchi

Department of Chemistry

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

89 Citations (Scopus)

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 language	English
Pages (from-to)	7238-7239
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	21
DOIs	https://doi.org/10.1021/ja902829p
Publication status	Published - 2009 Jun 3

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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.",

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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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