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成对电催化使亚磺酰胺与烯烃交叉偶联用于乙烯基亚砜亚胺的合成

Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines.

作者信息

Liu Tao, Tang Yan, Guo Jiyuan, Hang Yunfei, Zhang Kali, Zheng Changdi, Zhong Weihui, Song Dingguo, Ling Fei

机构信息

College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.

Zhejiang Hisoar Pharmaceutical Company, Ltd., Taizhou 318000, People's Republic of China.

出版信息

Org Lett. 2024 Oct 11;26(40):8463-8467. doi: 10.1021/acs.orglett.4c02859. Epub 2024 Oct 2.

DOI:10.1021/acs.orglett.4c02859
PMID:39356466
Abstract

We present here a novel paired electrocatalysis-enabled convenient synthesis of the ()-vinyl sulfoximines through the cross-coupling reaction of sulfinamides and olefins. This protocol showed a broad substrate scope and excellent selectivity of products under metal- and oxidant-free conditions. A preliminary mechanistic study suggested that fluorinated sulfoximine generated from anodic oxidation of sulfinamide was the key intermediate that was then converted into the sulfonimidoyl radical at the cathode with the help of DBU in this reaction.

摘要

我们在此展示了一种新颖的配对电催化方法,通过亚磺酰胺与烯烃的交叉偶联反应,实现了()-乙烯基亚砜亚胺的便捷合成。该方案在无金属和无氧化剂的条件下,展现出广泛的底物范围和优异的产物选择性。初步机理研究表明,亚磺酰胺阳极氧化生成的氟化亚砜亚胺是关键中间体,在该反应中,它随后在DBU的帮助下于阴极转化为磺酰亚胺基自由基。

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