Electrochemically Promoted Three-Component Synthesis for the Functionalization of <i>N</i>-Sulfonylformamidine

A one-pot synthetic strategy was developed by using electrochemical methods to convert sulfonamides into <i>N</i>-sulfonylformamidines, followed by the direct functionalization of the C-H bond through Shono oxidation. Subsequently, modification was achieved by introducing azide groups via imide ions under Lewis acid catalysis, utilizing TMSN<sub>3</sub> as the nucleophilic reagent. This strategy is compatible with a wide range of functional groups, and its utility has been demonstrated through scale-up experiments and derivatization reactions.

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Journal
The Journal of Organic Chemistry
Published
2025-08-27
DOI
https://doi.org/10.1021/acs.joc.5c01686
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.00

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article

Electrochemically Promoted Three-Component Synthesis for the Functionalization of N-Sulfonylformamidine

Li‐Rong Wen, Lin‐Bao Zhang, Weisi Guo, Li-Ming Zhang et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Electrochemically Promoted Three-Component Synthesis for the Functionalization of N-Sulfonylformamidine

Li‐Rong Wen, Lin‐Bao Zhang, Weisi Guo, Li-Ming Zhang, Yi-Le Song, Shi-Jie Bo, Ming Li, Jiaxiu Liu, Xue-Yang Guo
article en

Abstract

A one-pot synthetic strategy was developed by using electrochemical methods to convert sulfonamides into <i>N</i>-sulfonylformamidines, followed by the direct functionalization of the C-H bond through Shono oxidation. Subsequently, modification was achieved by introducing azide groups via imide ions under Lewis acid catalysis, utilizing TMSN<sub>3</sub> as the nucleophilic reagent. This strategy is compatible with a wide range of functional groups, and its utility has been demonstrated through scale-up experiments and derivatization reactions.

The Journal of Organic ChemistryVol. 90(36)
Qingdao University of Science and Technology (CN), State Key Laboratory of Chemical Engineering (CN)
National Natural Science Foundation of China, Natural Science Foundation of Shandong Province, Science and Technology Support Plan for Youth Innovation of Colleges and Universities of Shandong Province of China
Openalex Percentile: Top 83%
Sulfur-Based Synthesis Techniques
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