29945-53-7Relevant articles and documents
C-H arylation and alkenylation of imidazoles by nickel catalysis: Solvent-accelerated imidazole C-H activation
Muto, Kei,Hatakeyama, Taito,Yamaguchi, Junichiro,Itami, Kenichiro
, p. 6792 - 6798 (2015/11/24)
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.
C-H bonds as ubiquitous functionality: Preparation of multiple regioisomers of arylated 1,2,4-triazoles via C-H arylation
Joo, Jung Min,Guo, Pengfei,Sames, Dalibor
, p. 738 - 743 (2013/02/25)
We describe a general approach for the synthesis of complex aryl 1,2,4-triazoles. The electronic character of the C-H bonds and the triazole ring allows for the regioselective C-H arylation of 1-alkyl- and 4-alkyltriazoles under catalytic conditions. We have also developed the SEM and THP switch as well as trans-N-alkylation, which enable sequential arylation of the triazole ring to prepare 3,5-diaryltriazoles. This new strategy provides rapid access to a variety of arylated 1,2,4-triazoles and well complements existing cyclization methods.
A general method for copper-catalyzed arylation of arene C-H bonds
Do, Hien-Quang,Khan, Rana M. Kashif,Daugulis, Olafs
supporting information; experimental part, p. 15185 - 15192 (2009/03/12)
A general method for copper-catalyzed arylation of sp2 C-H bonds with pKa's below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K3PO4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups on a benzene ring can also be arylated. Two arylcopper-phenanthroline complex intermediates were independently synthesized.