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1-Bromoethene-1-sulfonyl fluoride (1-Br-ESF), a new SuFEx clickable reagent, and its application for regioselective construction of 5-sulfonylfluoro isoxazoles†
Chemical Communications ( IF 4.3 ) Pub Date : 2018-04-05 00:00:00 , DOI: 10.1039/c8cc00986d
Jing Leng 1, 2, 3, 4, 5 , Hua-Li Qin 1, 2, 3, 4, 5
Affiliation  

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.

中文翻译:

一种新型SuFEx可点击试剂1-溴乙烯-1-磺酰氟(1-Br-ESF)及其在5-磺酰氟异恶唑的区域选择性构建中的应用

开发了一种新的氟磺酰化试剂1-溴乙烯-1-磺酰氟(1-Br-ESF)。这种独特的试剂具有三个可寻址的手柄(乙烯基,溴化物和磺酰氟),并且具有巨大的潜力,可以用作三亲电子试剂和硫(VI)氟化物交换(SuFEx)可点击材料,以丰富SuFEx工具柜。通过与N-羟基苯甲酰亚胺基氯进行[3 + 2]环加成反应,已经实现了该试剂在5-磺酰基氟异恶唑的区域选择性合成中的应用。该实用方案提供了具有磺酰氟部分的官能化异恶唑的一般直接途径。
更新日期:2018-04-05
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