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.
Diao
Xiaoqiong
X
Department of Chemistry, Fudan University, Shanghai 200433, China.
Wang
Yuji
Y
Jiang
Yongwen
Y
Ma
Dawei
D
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