Cu(I)- or Ag(I)-Catalyzed Regio- and Stereocontrolled trans -Hydrofluorination of Ynamides

作者：Guangke He, Shineng Qiu, Hai Huang, Guohao Zhu, Dongming Zhang, Rong Zhang, Hongjun Zhu · 发表于：Organic Letters · 年份：2016 · DOI：10.1021/acs.orglett.6b00615 · 被引用次数：70 · 研究领域：Fluorine in Organic Chemistry、Cyclopropane Reaction Mechanisms、Catalytic Alkyne Reactions

With Et3N·3HF as the fluorinating reagent, a copper(I)- or silver(I)-catalyzed β/α-site-regiocontrolled trans-hydrofluorination of alkynamides has been achieved, affording the corresponding fluoro enamides in moderate to nearly quantitative yields with high regio- and stereoselectivity, respectively. The reaction proceeds under mild reaction conditions and exhibits good functional group tolerance. Further, the deuterium-labeling experiment confirmed the existence of the alkenylcopper intermediate.