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光诱导β,γ-不饱和酮与硫代磺酸盐的1,3-硫代磺酰化反应

Light-Induced 1,3-Thiosulfonylation of β,γ-Unsaturated Ketones with Thiosulfonates.

作者信息

Xu Jiuwen, Liu Bo-Xi, Liu Xin-Yu, Rao Weidong, Wang Shun-Yi

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China.

Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.

出版信息

Org Lett. 2024 Aug 16;26(32):6798-6802. doi: 10.1021/acs.orglett.4c01925. Epub 2024 Aug 7.

Abstract

Sulfur-containing compounds exhibit potent significance in drug molecules. Thiosulfonates as 1,3-thiosulfonylation reactants to olefins have yet to be investigated. Herein, we report photoinduced 1,3-difunctionalization of β,γ-unsaturated ketones with thiosulfonates, which undergo a radical 1,2-acyl shift. The protocol features mild conditions, high regioselectivity, and 100% atom economy.

摘要

含硫化合物在药物分子中具有重要意义。硫代磺酸酯作为烯烃的1,3-硫代磺酰化反应物尚未得到研究。在此,我们报道了硫代磺酸酯对β,γ-不饱和酮的光诱导1,3-双官能化反应,该反应经历自由基1,2-酰基迁移。该方法具有条件温和、区域选择性高和100%原子经济性的特点。

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