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

Xiaoqiong Diao, Yuji Wang, Yongwen Jiang and Dawei Ma*

*Department of Chemistry, Fudan University, Shanghai 200433, China, Email: madwmail.sioc.ac.cn

X. Diao, Y. Wang, Y. Jiang, D. Ma, J. Org. Chem., 2009, 74, 7974-7977.

DOI: 10.1021/jo9017183

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Abstract

CuI/l-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates affords 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.

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Key Words

benzimidazoles, benzimidazolones

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ID: J42-Y2009-3000