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

We present here a novel paired electrocatalysis-enabled convenient synthesis of the (E)-vinyl sulfoximines through the cross-coupling reaction of sulfinamides and olefins. This protocol showed a broad substrate scope and excellent E selectivity of products under metal- and oxidant-free conditions. A...

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Bibliographic Details
Published in:Organic letters 2024-10, Vol.26 (40), p.8463-8467
Main Authors: Liu, Tao, Tang, Yan, Guo, Jiyuan, Hang, Yunfei, Zhang, Kali, Zheng, Changdi, Zhong, Weihui, Song, Dingguo, Ling, Fei
Format: Article
Language:English
Subjects:
cathodes
cross-coupling reactions
oxidation
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Summary:We present here a novel paired electrocatalysis-enabled convenient synthesis of the (E)-vinyl sulfoximines through the cross-coupling reaction of sulfinamides and olefins. This protocol showed a broad substrate scope and excellent E 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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02859