Highly efficient copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides.
New (S)-pyrrolidinylmethylimidazole ligands (4a-c) have been readily synthesized in a straightforward fashion from least expensive starting materials in short steps in high yields. Relatively mild and highly efficient CuI-catalyzed N-arylation procedures for imidazoles with aryl and heteroaryl bromides or chlorides have been developed in the presence of 4a and Cs2CO3. It is important to note that the protocol could tolerate functional groups such as ester, nitrile, nitro, ketone, free hydroxyl, and free primary amine on the aryl halide. The protocol could also be applicable to other pi-electron-rich nitrogen heterocycles (pyrrole, pyrazole, indole, benzimidazole, and triazole), affording the N-arylazoles in good to excellent yields.
Zhu
Liangbo
L
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064, People's Republic of China.
Cheng
Liang
L
Zhang
Yuxi
Y
Xie
Rugang
R
You
Jingsong
J
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry
D006846:Hydrocarbons, Halogenated; D007093:Imidazoles; D007454:Iodides; D011720:Pyrazoles; D011758:Pyrroles; D014230:Triazoles; C031280:pyrazole; D003300:Copper; D009584:Nitrogen