1-Bromoethene-1-sulfonyl fluoride (1-Br-ESF), a new SuFEx clickable reagent, and its application for regioselective construction of 5-sulfonylfluoro isoxazoles
1-Bromoethene-1-sulfonyl fluoride (1-Br-ESF), a new SuFEx clickable reagent, and its application for regioselective construction of 5-sulfonylfluoro isoxazoles
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1-溴乙烯-1-磺酰氟（1-Br-ESF），一种新型SuFEx可点击试剂，及其在区域选择性构建5-磺酰氟异恶唑中的应用
DOI：
10.1039/c8cc00986d
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发表时间：
2018-04-28
影响因子：
4.9
通讯作者：
Qin, Hua-Li
中科院分区：
文献类型：
--
作者：
Leng, Jing;Qin, Hua-Li
合成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），具有很大的潜力，可用作三亲电试剂和硫（VI）氟化物交换（SuFEx）可点击材料，以丰富SuFEx工具柜。该试剂与N-羟基苯甲亚胺酰氯通过[3+2]环加成反应实现了5-磺酰基氟异恶唑的区域选择性合成。这个实用的方案提供了一种通用且直接的途径来获得具有磺酰氟部分的官能化异恶唑。
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.