抄録
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.
| 元の言語 | English |
|---|---|
| ページ（範囲） | 6792-6798 |
| ページ数 | 7 |
| ジャーナル | Chemical Science |
| 巻 | 6 |
| 発行部数 | 12 |
| DOI | |
| 出版物ステータス | Published - 2015 |
| 外部発表 | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
これを引用
C-H arylation and alkenylation of imidazoles by nickel catalysis : Solvent-accelerated imidazole C-H activation. / Muto, Kei; Hatakeyama, Taito; Yamaguchi, Junichiro; Itami, Kenichiro.
：: Chemical Science, 巻 6, 番号 12, 2015, p. 6792-6798.研究成果: Article
}
TY - JOUR
T1 - C-H arylation and alkenylation of imidazoles by nickel catalysis
T2 - Solvent-accelerated imidazole C-H activation
AU - Muto, Kei
AU - Hatakeyama, Taito
AU - Yamaguchi, Junichiro
AU - Itami, Kenichiro
PY - 2015
Y1 - 2015
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84946911435&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84946911435&partnerID=8YFLogxK
U2 - 10.1039/c5sc02942b
DO - 10.1039/c5sc02942b
M3 - Article
AN - SCOPUS:84946911435
VL - 6
SP - 6792
EP - 6798
JO - Chemical Science
JF - Chemical Science
SN - 2041-6520
IS - 12
ER -