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 | |
| Publication status | Published - 2009 Jun 3 |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Cleavage of C-N bonds in aniline derivatives on a ruthenium center and its relevance to catalytic C-C bond formation. / Koreeda, Tetsuro; Kochi, Takuya; Kakiuchi, Fumitoshi.
In: Journal of the American Chemical Society, Vol. 131, No. 21, 03.06.2009, p. 7238-7239.Research output: Contribution to journal › Article
}
TY - JOUR
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.
UR - http://www.scopus.com/inward/record.url?scp=67650566924&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=67650566924&partnerID=8YFLogxK
U2 - 10.1021/ja902829p
DO - 10.1021/ja902829p
M3 - Article
C2 - 19432447
AN - SCOPUS:67650566924
VL - 131
SP - 7238
EP - 7239
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 21
ER -