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 |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
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Muto, K., Yamaguchi, J., Lei, A., & Itami, K. (2013). Isolation, structure, and reactivity of an arylnickel(II) pivalate complex in catalytic C-H/C-O biaryl coupling. Journal of the American Chemical Society, 135(44), 16384-16387. https://doi.org/10.1021/ja409803x