A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an "F-SO2+" Donor of Unprecedented Reactivity, Selectivity, and Scope
A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an "F-SO2+" Donor of Unprecedented Reactivity, Selectivity, and Scope
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SuFEx 点击化学的新门户：稳定的氟硫基咪唑鎓盐作为“F-SO2”供体出现，具有前所未有的反应性、选择性和范围
DOI：
10.1002/anie.201712429
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发表时间：
2018-03-01
影响因子：
16.6
通讯作者：
Dong, Jiajia
中科院分区：
文献类型：
--
作者：
Guo, Taijie;Meng, Genyi;Dong, Jiajia
硫酰氟，SO2 F2，已被发现在各种环境中的酚类衍生化，即使是那些在高功能分子。我们现在报告，固体氟磺酰基咪唑鎓三氟甲磺酸盐提供相同的F-SO2+片段的Nu-H受体基团在基板上。然而，这种三氟甲磺酸盐是比SO2 F2反应性更强的氟磺酰化剂，并显示出其自身的选择性偏好。此外，新的三氟甲磺酸唑鎓试剂在反应停止之前与伯胺和苯胺反应一次。另一方面，与三乙胺和两个当量的F-SO 2+供体存在，它进行到双（氟磺酰基）酰亚胺在良好的收率，两个重要的转换，我们从来没有见过的硫酰氟作为亲电试剂。
Sulfuryl fluoride, SO2F2, has been found to derivatize phenols in all kinds of environments, even those in highly functional molecules. We now report that a solid fluorosulfuryl imidazolium triflate salt delivers the same F-SO2+ fragment to Nu-H acceptor groups in the substrates. However, this triflate salt is a far more reactive fluorosulfurylating agent than SO2F2 and displays selectivity preferences of its own. Moreover, the new azolium triflate reagent reacts once with primary amines and anilines before the reaction stops. On the other hand, with triethylamine and two equivalents of the F-SO2+ donor present, it proceeds on to the bis(fluorosulfuryl)imides in good yieldtwo important conversions that we have never seen with sulfuryl fluoride as the electrophile.