C–H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C–H activation
- ️Kenichiro Itami
* Corresponding authors
a
Institute of Transformative Bio-Molecules (WPI-ITbM) and Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
E-mail:
itami@chem.nagoya-u.ac.jp, junichiro@chem.nagoya-u.ac.jp
b Central Research Laboratory Technology and Development Division, Kanto Chemicals Co. Inc., Saitama 340-0003, Japan
c JST, ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602, Japan
Abstract
The first nickel-catalyzed C–H arylations and alkenylations of imidazoles with phenol and enol derivatives are described. Under the influence of Ni(OTf)2/dcype/K3PO4 (dcype: 1,2-bis(dicyclohexylphosphino)ethane) in t-amyl alcohol, imidazoles can undergo C–H arylation with phenol derivatives. The C–H arylation of imidazoles with chloroarenes as well as that of thiazoles and oxazoles with phenol derivatives can also be achieved with this catalytic system. By changing the ligand to dcypt (3,4-bis(dicyclohexylphosphino)thiophene), enol derivatives could also be employed as coupling partners achieving the C–H alkenylation of imidazoles as well as thiazoles and oxazoles. Thus, a range of C2-arylated and alkenylated azoles can be synthesized using this newly developed nickel-based catalytic system. The key to the success of the C–H coupling of imidazoles is the use of a tertiary alcohol as solvent. This also allows the use of an air-stable nickel(II) salt as the catalyst precursor.
Supplementary files
Article information
- https://doi.org/10.1039/C5SC02942B
- Edge Article
- 10 Aug 2015
- 07 Sep 2015
- 08 Sep 2015
-
DOI
Article type
Submitted
Accepted
First published
All publication charges for this article have been paid for by the Royal Society of Chemistry
Chem. Sci., 2015,6, 6792-6798
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C–H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C–H activation
K. Muto, T. Hatakeyama, J. Yamaguchi and K. Itami, Chem. Sci., 2015, 6, 6792 DOI: 10.1039/C5SC02942B
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