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

Xiang-Rui Li,^aWen-Xin Li,^aZhuo-Wen Zhang,^aChuanji Shen,^bXiaocong Zhou,*^,bXue-Qiang Chu,^aWeidong Rao,^cZhi-Liang Shen*^,a

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

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

^cJiangsu 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 99:1Z/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