Abstract
We describe mechanistic studies of a C-H/C-O biaryl coupling of 1,3-azoles and aryl pivalates catalyzed by Ni(cod)2/dcype. This study not only supports a catalytic cycle consisting of C-O oxidative addition, C-H nickelation, and reductive elimination but also provides insight into the dramatic ligand effect in C-H/C-O coupling. We have achieved the first synthesis, isolation and structure elucidation of an arylnickel(II) pivalate, which is an intermediate in the catalytic cycle after oxidative addition of a C-O bond. Furthermore, kinetic studies and kinetic isotope effect investigations reveal that the C-H nickelation is the turnover-limiting step in the catalytic cycle.
| Original language | English |
|---|---|
| Pages (from-to) | 16384-16387 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 135 |
| Issue number | 44 |
| DOIs | |
| Publication status | Published - 2013 Nov 6 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Isolation, structure, and reactivity of an arylnickel(II) pivalate complex in catalytic C-H/C-O biaryl coupling. / Muto, Kei; Yamaguchi, Junichiro; Lei, Aiwen; Itami, Kenichiro.
In: Journal of the American Chemical Society, Vol. 135, No. 44, 06.11.2013, p. 16384-16387.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Isolation, structure, and reactivity of an arylnickel(II) pivalate complex in catalytic C-H/C-O biaryl coupling
AU - Muto, Kei
AU - Yamaguchi, Junichiro
AU - Lei, Aiwen
AU - Itami, Kenichiro
PY - 2013/11/6
Y1 - 2013/11/6
N2 - We describe mechanistic studies of a C-H/C-O biaryl coupling of 1,3-azoles and aryl pivalates catalyzed by Ni(cod)2/dcype. This study not only supports a catalytic cycle consisting of C-O oxidative addition, C-H nickelation, and reductive elimination but also provides insight into the dramatic ligand effect in C-H/C-O coupling. We have achieved the first synthesis, isolation and structure elucidation of an arylnickel(II) pivalate, which is an intermediate in the catalytic cycle after oxidative addition of a C-O bond. Furthermore, kinetic studies and kinetic isotope effect investigations reveal that the C-H nickelation is the turnover-limiting step in the catalytic cycle.
AB - We describe mechanistic studies of a C-H/C-O biaryl coupling of 1,3-azoles and aryl pivalates catalyzed by Ni(cod)2/dcype. This study not only supports a catalytic cycle consisting of C-O oxidative addition, C-H nickelation, and reductive elimination but also provides insight into the dramatic ligand effect in C-H/C-O coupling. We have achieved the first synthesis, isolation and structure elucidation of an arylnickel(II) pivalate, which is an intermediate in the catalytic cycle after oxidative addition of a C-O bond. Furthermore, kinetic studies and kinetic isotope effect investigations reveal that the C-H nickelation is the turnover-limiting step in the catalytic cycle.
UR - http://www.scopus.com/inward/record.url?scp=84887638677&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84887638677&partnerID=8YFLogxK
U2 - 10.1021/ja409803x
DO - 10.1021/ja409803x
M3 - Article
C2 - 24152083
AN - SCOPUS:84887638677
VL - 135
SP - 16384
EP - 16387
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 44
ER -