Yan Zhenxing, Ye Jie, Wang Heng, Chen Tao, Xu Ze-Feng, Yu Mingming, Li Chuan-Ying
School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, China.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Org Lett. 2024 Aug 9;26(31):6647-6651. doi: 10.1021/acs.orglett.4c02303. Epub 2024 Jul 29.
Readily accessible -sulfonylaminophthalimides were developed to be efficient sulfonyl radical precursors upon being treated with a base/oxidant under mild conditions. The method was applied to the oxysulfonylation of olefins, providing β-ketosulfones and isobenzofurans stereoselectively. On the basis of control experiments, density functional theory calculations, and the literature, a plausible radical mechanism was proposed. The findings offered a chance to develop novel radical precursors based on diversely substituted -aminophthalimides, which might establish a universal mild approach for the generation of various radicals.
易于获得的磺酰氨基邻苯二甲酰亚胺被开发为在温和条件下用碱/氧化剂处理时有效的磺酰基自由基前体。该方法应用于烯烃的氧磺酰化反应，立体选择性地提供β-酮砜和异苯并呋喃。基于对照实验、密度泛函理论计算和文献，提出了一种合理的自由基机理。这些发现为基于不同取代的氨基邻苯二甲酰亚胺开发新型自由基前体提供了机会，这可能为生成各种自由基建立一种通用的温和方法。
