NDLI: C–H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C

Content Provider	Royal Society of Chemistry (RSC)
Author	Hatakeyama, Taito Yamaguchi, Junichiro Itami, Kenichiro Muto, Kei
Copyright Year	2015
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.
Starting Page	6792
Ending Page	6798
Page Count	7
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	6
Issue Number	12
Journal	Chemical Science
DOI	10.1039/c5sc02942b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Phenol Ligand Enol Nickel Aryl Thiophene Solvent
Content Type	Text
Resource Type	Article
Subject	Chemistry

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C–H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C–H activation