Assembly of substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones via CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates.
CuI/l-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates affords the aryl amination products at room temperature, which undergo in situ additive cyclization under acidic conditions or heating to give substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones, respectively. A wide range of functional groups including ketone, nitro, iodo, bromo, and ester are tolerated under these reaction conditions, providing these heterocycles with great diversity.
Department of Chemistry, Fudan University, Shanghai 200433, China.
Xiaoqiong
X
Diao
Yuji
Y
Wang
Yongwen
Y
Jiang
Dawei
D
Ma
D000083:Acetanilides / Q000737:chemistry; D000641:Ammonia / Q000737:chemistry*; D001562:Benzimidazoles / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D048448:Phenylcarbamates / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000083:Acetanilides; D001562:Benzimidazoles; D007454:Iodides; D048448:Phenylcarbamates; D014867:Water; D000641:Ammonia; D003300:Copper; C073870:cuprous iodide; D007455:Iodine; D011392:Proline