Leng Jing, Qin Hua-Li
School of Chemistry, Chemical Engineering and Life Science, and State Key Laboratory of Silicate Materials for Architectures Wuhan University of Technology, 205 Luoshi Road, Wuhan, Hubei Province 430070, P. R. China.
Chem Commun (Camb). 2018 Apr 26;54(35):4477-4480. doi: 10.1039/c8cc00986d.
A new fluorosulfonylation reagent 1-bromoethene-1-sulfonyl fluoride was developed (1-Br-ESF). This unique reagent possesses three addressable handles (vinyl, bromide, and sulfonyl fluoride) and has great potential to function as a tris-electrophile and as a sulfur(vi) fluoride exchange (SuFEx) clickable material to enrich the SuFEx tool cabinet. The application of this reagent for regioselective synthesis of 5-sulfonylfluoro isoxazoles has been realized through a [3+2] cycloaddition with N-hydroxybenzimidoyl chlorides. This practical protocol provides a general and direct route to functionalized isoxazoles possessing sulfonyl fluoride moieties.
一种新型氟磺酰化试剂1-溴乙烯-1-磺酰氟（1-Br-ESF）被开发出来。这种独特的试剂具有三个可修饰的官能团（乙烯基、溴和磺酰氟），并且作为三亲电试剂以及作为一种可用于硫（VI）氟交换（SuFEx）点击反应的材料具有巨大潜力，能够丰富SuFEx工具库。通过与N-羟基苯甲亚胺酰氯进行[3+2]环加成反应，实现了该试剂用于区域选择性合成5-磺酰氟异恶唑的应用。这一实用方法为合成含有磺酰氟基团的功能化异恶唑提供了一条通用且直接的途径。
