Bisulfite-mediated base-free decarboxylative carbonylsulfination of alkenes: access to β-keto sultines

IF 10.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Science China Chemistry Pub Date : 2024-09-24 DOI:10.1007/s11426-024-2210-2

Yongxin Zhang, Pan Zhou, Xinyue Ma, Xiaoxiao Yang, Xing Fang, Yuxi Wang, Chao Shu

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引用次数: 0

Abstract

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/SO₂ insertion/ionic cyclization relay process, distinct from traditional alkenes bifunctionalization.

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来源期刊

Science China Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

7.30%

发文量

3787

审稿时长

2.2 months

期刊介绍： Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field. Categories of articles include: Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry. Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies. Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.