Synthesis of Sulfenamides via Photoredox N–S Coupling of Dialkyl Azodicarboxylates and Thiols

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-27 DOI:10.1021/acs.orglett.4c04454
Qun Liu, Xiaoyun Feng, Fenghao Xie, Yingchao Lai, Haokun Jiang, Yujing Jiao, Jin Wang
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Abstract

We herein report a photoredox N–S coupling reaction between dialkyl azodicarboxylates and thiols to access sulfenamide scaffolds. This reaction proceeds under mild, green, and operationally simple conditions, offering a broad scope of sulfenamides with high yields and excellent atom efficiency. Mechanistic investigations revealed this reaction followed a photoinitiated radical pathway in which iodide plays a crucial role as both a radical initiator and a single-electron reductant.

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二烷基偶氮二羧酸盐与硫醇光氧化还原N-S偶联合成磺胺类化合物
我们在此报道了二烷基偶氮二羧酸盐和硫醇之间的光氧化还原N-S偶联反应,以获得亚胺支架。该反应在温和、绿色和操作简单的条件下进行,可获得广泛的亚胺类化合物,收率高,原子效率高。机理研究表明,该反应遵循光引发自由基途径,其中碘化物作为自由基引发剂和单电子还原剂起关键作用。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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