C-H arylation and alkenylation of imidazoles by nickel catalysis

Solvent-accelerated imidazole C-H activation

Kei Muto, Taito Hatakeyama, Junichiro Yamaguchi, Kenichiro Itami

Research output: Contribution to journalArticle

56 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)6792-6798
Number of pages7
JournalChemical Science
Volume6
Issue number12
DOIs
Publication statusPublished - 2015
Externally publishedYes

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Alkenylation
Imidazoles
Nickel
Catalysis
Chemical activation
Phenol
Oxazoles
Derivatives
Thiazoles
Thiophenes
Azoles
Ethane
Salts
Alcohols
imidazole
Ligands
Catalysts
Air

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

C-H arylation and alkenylation of imidazoles by nickel catalysis : Solvent-accelerated imidazole C-H activation. / Muto, Kei; Hatakeyama, Taito; Yamaguchi, Junichiro; Itami, Kenichiro.

In: Chemical Science, Vol. 6, No. 12, 2015, p. 6792-6798.

Research output: Contribution to journalArticle

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