(IPr)CuF-catalyzed α-site regiocontrolled trans-hydrofluorination of ynamides

作者：Guohao Zhu, Shineng Qiu, Yang Xi, Yao Ding, Dongming Zhang, Rong Zhang, Guangke He, Hongjun Zhu · 发表于：Organic & Biomolecular Chemistry · 年份：2016 · DOI：10.1039/c6ob01345g · 被引用次数：39 · 研究领域：Fluorine in Organic Chemistry、Cyclopropane Reaction Mechanisms、Carbon dioxide utilization in catalysis

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.