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通过铜和可见光诱导的叠氮化物与 S(O)-H 键偶联构建苯磺酰胺衍生物。

Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)-H Coupling.

机构信息

Nantong Key Laboratory of Heterocycles, School of Chemistry and Chemical Engineering of Nantong University, Nantong 226019, China.

出版信息

Molecules. 2022 Aug 28;27(17):5539. doi: 10.3390/molecules27175539.

DOI:10.3390/molecules27175539
PMID:36080306
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9457716/
Abstract

We here have developed an S(O)-N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis. In this efficient and mild pathway, the reaction produces sulfonamide compounds under redox-neutral condition, which is mechanistically different from the nitrogen nucleophilic substitution reactions. Significantly, this transformation intends to utilize the property of visible light-induced azides to generate triplet nitrene and followed coupling with sulfonyl radicals in situ to achieve structurally diverse benzenesulfinamides in good yields.

摘要

我们在此通过双铜和可见光催化发展了苯亚磺酸钠衍生物和芳基叠氮之间的 S(O)-N 偶联。在这种高效和温和的反应途径中,反应在氧化还原中性条件下生成磺酰胺化合物,这在机理上不同于氮亲核取代反应。值得注意的是,这种转化旨在利用可见光诱导的叠氮化物生成三重态氮烯的特性,并随后与亚磺酰基自由基原位偶联,以良好的收率得到结构多样的苯磺酰胺。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/a1faf1ebaf18/molecules-27-05539-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/bb189c751950/molecules-27-05539-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/cb5aa17dd804/molecules-27-05539-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/8b5ed718e72f/molecules-27-05539-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/a1faf1ebaf18/molecules-27-05539-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/bb189c751950/molecules-27-05539-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/cb5aa17dd804/molecules-27-05539-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/8b5ed718e72f/molecules-27-05539-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b372/9457716/a1faf1ebaf18/molecules-27-05539-sch003.jpg

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本文引用的文献

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