Stereoselective Synthesis of Fluoroalkylated (Z)-Alkene via Nickel-Catalyzed and Iron-Mediated Hydrofluoroalkylation of Alkynes

Xiang-Rui Li,^a Wen-Xin Li,^a Zhuo-Wen Zhang,^a Chuanji Shen,^b Xiaocong Zhou,*^,b Xue-Qiang Chu,^a Weidong Rao,^c Zhi-Liang Shen*^,a

^a Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

^b College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, China.

^c Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

Abstract: An efficient nickel-catalyzed, iron-mediated hydrofluoroalkylation of alkynes with bromodifluoroacetate or perfluoroalkyl iodide was developed. The reactions proceeded efficiently via a radical reaction pathway to give fluoroalkylated (Z)-alkenes in moderate to good yields with good control of stereoselectivity (up to 99:1 Z/E), exhibiting both wide substrate scope and broad functional group tolerance. In addition, the method also entailed the easy functionalization of alkyne-tethered complex molecules derived from sugars and pharmaceuticals.

Org. Chem. Front. 2021, 8, 6377–6383. (Impact factor: 5.281)

论文链接：https://pubs.rsc.org/en/Content/ArticleLanding/2021/QO/D1QO00983D