Bisulfite-mediated base-free decarboxylative carbonylsulfination of alkenes:access to β-keto sultines
作者机构：State Key Laboratory of Green Pesticide Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction CCNU-uOttawa Joint Research Centre College of Chemistry Central China Normal University (CCNU) Key Laboratory of Functional Molecular Solids Ministry of Education Anhui Normal University
出 版 物：《Science China Chemistry》 (中国科学:化学(英文版))
年 卷 期：2024年
核心收录：
学科分类：081704[工学-应用化学] 081705[工学-工业催化] 07[理学] 070304[理学-物理化学(含∶化学物理)] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
基 金：supported by the National Key R&D Program of China (2023YFD1700500) the National Natural Science Foundation of China (22301093) the Fundamental Research Funds for the Central Universities,the Central China Normal University (CCNU) the Knowledge Innovation Program of Wuhan-Shuguang Project
摘 要：A straightforward three-component decarboxylative cross-coupling of α-keto acids, alkenes and sodium bisulfite is established for the construction of otherwise challenging-to-access β-keto sultine derivatives. This reaction involves the photoinduced carbonylsulfination of alkenes and utilizes sodium bisulfite as both a sulfur dioxide surrogate and buffer agent for deprotonation of α-keto carboxylic acids. Of note, the practical procedure featured broad substrate scope and group tolerance for diverse biologically important molecules under mild and operationally simple conditions, using an organic photocatalyst. Mechanistic studies indicated that the transformation proceeds an apparent two-pronged radical addition/radical-polar crossover/SO2insertion/ionic cyclization relay process, distinct from traditional alkenes bifunctionalization.
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