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通过光氧化还原和 -杂环卡宾催化的烯烃与二硫化合物和醛的自由基接力反应实现β-硫代-α-芳基酮的合成。

Synthesis of β-Thiolated-α-arylated Ketones Enabled by Photoredox and -Heterocyclic Carbene-Catalyzed Radical Relay of Alkenes with Disulfides and Aldehydes.

机构信息

Shenzhen Grubbs Institute, Department of Chemistry, and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong 518055, P. R. China.

出版信息

Org Lett. 2022 Aug 5;24(30):5519-5524. doi: 10.1021/acs.orglett.2c01915. Epub 2022 Jul 21.

Abstract

β-Thiolated-α-arylated ketones are perversive in bioactive molecules and serve as potential bidentate ligands for catalysis. Herein, a straightforward protocol to access β-thiolated ketones from aldehydes, alkenes, and disulfides enabled by the combination of photocatalysis and -heterocyclic carbene catalysis is reported. The sequential radical addition to alkenes and subsequent radical-radical coupling cascade process simultaneously forge C-S and C-C bonds. The mild conditions allow for radical relay coupling with a broad functional group tolerance.

摘要

β-硫代-α-芳基酮在生物活性分子中很反常,可用作催化的潜在双齿配体。在此,我们报告了一种通过光催化和 -杂环卡宾催化相结合,从醛、烯烃和二硫化物直接制备β-硫代酮的方法。该方法通过自由基加成到烯烃上,然后进行自由基-自由基偶联级联反应,同时构建 C-S 和 C-C 键。温和的反应条件允许进行自由基接力偶联,具有广泛的官能团容忍度。

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