Paired Electrocatalysis-Enabled\nCross Coupling of\nSulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

We present here a novel paired electrocatalysis-enabled\nconvenient\nsynthesis of the (<i>E</i>)-vinyl sulfoximines through the\ncross-coupling reaction of sulfinamides and olefins. This protocol\nshowed a broad substrate scope and excellent <i>E</i> selectivity\nof products under metal- and oxidant-free conditions. A preliminary\nmechanistic study suggested that fluorinated sulfoximine generated\nfrom anodic oxidation of sulfinamide was the key intermediate that\nwas then converted into the sulfonimidoyl radical at the cathode with\nthe help of DBU in this reaction.

Publication Details

Journal
Figshare
Published
2024-10-02
DOI
https://doi.org/10.1021/acs.orglett.4c02859.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Paired Electrocatalysis-Enabled\nCross Coupling of\nSulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

Figshare
Radical Photochemical Reactions
article

Paired Electrocatalysis-Enabled\nCross Coupling of\nSulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

article en

Abstract

We present here a novel paired electrocatalysis-enabled\nconvenient\nsynthesis of the (<i>E</i>)-vinyl sulfoximines through the\ncross-coupling reaction of sulfinamides and olefins. This protocol\nshowed a broad substrate scope and excellent <i>E</i> selectivity\nof products under metal- and oxidant-free conditions. A preliminary\nmechanistic study suggested that fluorinated sulfoximine generated\nfrom anodic oxidation of sulfinamide was the key intermediate that\nwas then converted into the sulfonimidoyl radical at the cathode with\nthe help of DBU in this reaction.

Figshare
Openalex Percentile: Top 75%
Radical Photochemical Reactions
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Paired Electrocatalysis-Enabled\nCross Coupling of\nSulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines · Figshare (2024) | TGRS Research Map | TGRS