La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia.
Chem Commun (Camb). 2018 Jun 8;54(47):6020-6023. doi: 10.1039/c8cc03400a.
We demonstrate 1,2-dibromoethane-1-sulfonyl fluoride (DESF) as a bench-stable and readily accessible precursor to the robust SuFEx connector, 1-bromoethene-1-sulfonyl fluoride (BESF). The in situ generation of BESF from DESF opens up several new reaction profiles, including application in the syntheses of unprecedented 3-substituted isoxazole-5-sulfonyl fluorides, 1-substituted-1H-1,2,3-triazole-4-sulfonyl fluorides, 2-amino-1-bromoethane-1-sulfonyl fluorides and 4-bromo-β-sultams in good to excellent yields. These new modules comprise a pendant sulfonyl fluoride handle, which further undergoes facile and selective SuFEx reactions with a selection of aryl silyl ethers to generate stable and useful sulfonate connections.
我们展示了 1,2-二溴乙烷-1-磺酰氟 (DESF) 作为一种稳定且易于获得的前体,可以转化为强大的 SuFEx 连接体,即 1-溴乙烯-1-磺酰氟 (BESF)。DESF 原位生成 BESF 开辟了几个新的反应途径,包括应用于前所未有的 3-取代异噁唑-5-磺酰氟、1-取代-1H-1,2,3-三唑-4-磺酰氟、2-氨基-1-溴乙烷-1-磺酰氟和 4-溴-β-内酰胺的合成,产率良好至优秀。这些新模块包含一个悬垂磺酰氟基团,它可以进一步与一系列芳基硅醚发生易于选择的 SuFEx 反应,生成稳定且有用的磺酸盐连接。