Photocatalyst-Free Activation of Sulfamoyl Chlorides for Regioselective Sulfamoyl-Oximation of Alkenes via Hydrogen Atom Transfer (HAT) and Halogen-Atom Transfer (XAT) Relay Strategy
作者:Wei Li、Zhihua Huang、Deliang Zhong、Huaifeng Li
DOI:10.1021/acs.orglett.4c00314
日期:2024.3.15
methodologies have been limited to either the use of photocatalyst or the monofunctionalization of activated alkenes. Here, we report a regioselective sulfamoyl-oximation of alkenes by involving the activation of sulfamoyl chlorides through a HAT and XAT relay strategy in a photocatalyst-free way. The key to this success lies in the dual roles of tert-butyl nitrite (TBN), which not only serves as the source
使用容易获得的多种氨磺酰氯来合成磺酰胺化合物是一种有趣但尚未充分探索的策略。由于氨磺酰氯的高还原电位,通过单电子还原激活氨磺酰氯面临着挑战。或者,氨磺酰氯中的SO 2 –Cl 键很容易被XAT 裂解。然而,现有的方法仅限于使用光催化剂或活化烯烃的单官能化。在这里,我们报道了烯烃的区域选择性氨磺酰肟化,通过 HAT 和 XAT 中继策略以无光催化剂的方式激活氨磺酰氯。这一成功的关键在于亚硝酸叔丁酯 (TBN) 的双重作用,它不仅充当肟的来源,还充当 HAT 试剂来生成关键的 XAT 反应物种。排除利用光能的金属催化剂或光敏剂使得该协议具有通用性并且普遍适用于合成各种结构多样的含肟的烷基磺酰胺。