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■ Efficient Synthesis of Fluorinated Benzimidazolines, Benzoxazolines and Benzothiazolines Catalyzed by Hf(Otf)4

Jing-Ying Wei, Shuai-Bo Han, Xiao-Chong Peng, Cheng-Jun Wang, De-Yun Zeng, Shan-Shan Gong,* and Qi Sun*

*Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Ave, Nanchang, Jiangxi Province, China

Abstract

Hafnium triflate was identified as a highly efficient catalyst for the synthesis of a diversity of fluorinated benzimidazolines, benzoxazolines, and benzothiozolines. For the first time, more complicated N-substituted benzimidazolines were synthesized via the Hf(OTf)4-catalyzed method. With the assistance of 19F NMR, the catalytic roles of Hf(IV) on the activation of fluorinated ketone and fluorinated imine intermediate were revealed.