Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 44, Pages 16384-16387Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja409803x
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Funding
- JSPS [220GR049]
- MEXT [25105720, 25708005]
- JSPS
- World Premier International Research Center (WPI) Initiative, Japan
- Grants-in-Aid for Scientific Research [25708005, 25105720, 13J03280] Funding Source: KAKEN
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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.
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