文献类型：期刊文献

英文题名：Enantioselective Fluorination of 2-Oxindoles by Structure-Micro-Tuned N-Fluorobenzenesulfonamides

作者：Wang, Fajie[1,2];Li, Juli[1,2];Hu, Qingyang[1,2];Yang, Xianjin[1,2,3];Wu, Xin-Yan[1,2];He, Haoming[4]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China;[4]Wengfu Grp Co Ltd, Hongfu 550000, Guizhou, Peoples R China

年份：2014

卷号：2014

期号：17

起止页码：3607

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000337693500015)】；

基金：The authors are grateful to the Chinese National Natural Science Foundation (NSFC) (grant number 21372077) for financial support.

语种：英文

外文关键词：Homogeneous catalysis; Palladium; Fluorine; Fluorination; Nitrogen heterocycles; Enantioselectivity

摘要：We describe our attempts to fine-tune the reactivity and selectivity of N-fluorobenzenesulfonamide in fluorination reactions by changing the substituents on its phenyl rings. A series of N-fluorobenzenesulfonamides bearing substituents at the ortho, meta, and para positions were prepared, and were used in the enantioselective fluorination of 2-oxindoles catalysed by chiral palladium complexes. Fluorinating reagents 1b, 1c, 1d, 1e, 1h, 1i, and 1j gave similar results to 1a, while 1f, 1g, and 1n gave worse yields and selectivities. Under mild reaction conditions, a series of 3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) using N-fluoro-4,4'-difluorobenzenesulfonamide as the fluorination agent.