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Published on: January 19, 2016
(IPr)CuF-catalyzed α-site regiocontrolled trans-hydrofluorination of ynamides
Guohao Zhu1, Shineng Qiu1, Yang Xi1
1Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, People' s Republic of China. hegk@njtech.edu.cn zhuhj@njtech.edu.cn.
Abstract:
With Et3N·3HF as the fluorination reagent, (IPr)CuF-catalyzed α-site regiocontrolled trans-hydrofluorination of ynamides has been achieved, affording (Z)-α-fluoroenamides in moderate to excellent yields. It was interesting to note that the regioselectivity of the reaction is reversed to that observed in the (Ph3P)3CuF-catalyzed hydrofluorination of ynamides. Additionally, a variety of different ynamides including oxazolidinonyl-, imidazolyl-, and N-sulfonyl ynamides were suitable for the reaction system and the subsequent oxidation of the fluorinated products enables a convenient synthesis to α-fluoroimides.
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