Palladium-Catalyzed Defluorinative Alkynylation of Polyfluoroalkyl Ketones with Alkynes for the Synthesis of Fluorinated Fused Furans

Xue-Qiang Chu,*^a Man-Ling Zhi,^a Si-Xuan Zhang,^a Ya-Wen Wang,^a Weidong Rao,^b Haiyan Xu,^c and Zhi-Liang Shen*^a

^a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China. E-mail: ias_zlshen@njtech.edu.cn; xueqiangchu@njtech.edu.cn.

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

^c School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, China.

Abstract: A Pd-catalyzed C-F bond alkynylation of polyfluoroalkyl ketones with terminal alkynes has been developed. The method gives access to a range of modular perfluoroalkyl- and alkynyl-substituted furan derivatives in moderate yields with high chemoselectivity and regioselectivity. Key to the success of the present cascade reaction mainly relies on the well-controlled sequence of multiple C(sp³)-F bond functionalization and alkynylation. Mechanistic studies showed that the reaction presumably proceeded through a chelation-assisted oxidative addition of Pd to C-F bond.

Organic Chemistry Frontiers 2021, 8, 572-578. (Impact factor: 5.155)

论文链接：https://pubs.rsc.org/en/content/articlelanding/2020/qo/d0qo01009j#!divAbstract