Photoredox Radical Truce–Smiles Rearrangement of <i>N-</i>Sulfinyl Acrylamides with Bromodifluoroacetamides

We herein report a photochemical Truce-Smiles rearrangement reaction of <i>N</i>-sulfinyl acrylamides with bromodifluoroacetamides resulting in the synthesis of a series of aryl difluoroglutaramides in moderate to good yields. The asymmetric synthesis using chiral sulfinamides produced quaternary carbon<i>-</i>centered glutaramide products with a modest enantioselectivity. This protocol effectively complements previous Truce-Smiles rearrangement methods involving <i>N</i>-sulfonyl acrylamides.

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Publication Details

Journal
Organic Letters
Published
2024-12-18
DOI
https://doi.org/10.1021/acs.orglett.4c04484
Citations
14
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
3.50

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article

Photoredox Radical Truce–Smiles Rearrangement of N-Sulfinyl Acrylamides with Bromodifluoroacetamides

Xiaochen Ji, Huawen Huang, Lin Tian, Guo‐Jun Deng et al.
14 citations
Organic Letters
Radical Photochemical Reactions
3.50
article

Photoredox Radical Truce–Smiles Rearrangement of N-Sulfinyl Acrylamides with Bromodifluoroacetamides

Xiaochen Ji, Huawen Huang, Lin Tian, Guo‐Jun Deng, Pu Chen
article en
14 citations

Abstract

We herein report a photochemical Truce-Smiles rearrangement reaction of <i>N</i>-sulfinyl acrylamides with bromodifluoroacetamides resulting in the synthesis of a series of aryl difluoroglutaramides in moderate to good yields. The asymmetric synthesis using chiral sulfinamides produced quaternary carbon<i>-</i>centered glutaramide products with a modest enantioselectivity. This protocol effectively complements previous Truce-Smiles rearrangement methods involving <i>N</i>-sulfonyl acrylamides.

Organic LettersVol. 27(1)
Xiangtan University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hunan Province
Openalex Percentile: Top 7%
Radical Photochemical Reactions
3.50
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