Photoredox-Catalyzed Deconstructive Sulfinamidation of Pro-Aromatic Carbocycles: A Sustainable Approach

Sulfinamides make up a class of valuable chemicals with broad applications in organic synthesis and pharmaceutical research. Herein, we report a photocatalytic method for the straightforward synthesis of functionalized alkylsulfinamides from spiro pro-aromatic carbocycles with excellent atom economy. A variety of pro-aromatic carbocycles readily undergo C-C bond cleavage/sulfinamidation with <i>N</i>-sulfinylamines, yielding distally and site-specifically heteroarylated alkylsulfinamides with excellent yields and remarkable functional group tolerance. Mechanism studies indicate a radical pathway for this transformation.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-09-25
DOI
https://doi.org/10.1021/acs.joc.5c01834
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
1.87
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article

Photoredox-Catalyzed Deconstructive Sulfinamidation of Pro-Aromatic Carbocycles: A Sustainable Approach

Li‐Na Guo, Hong-Jie Miao, Xin‐Hua Duan, Hongfei Liu et al.
2 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
1.87
article

Photoredox-Catalyzed Deconstructive Sulfinamidation of Pro-Aromatic Carbocycles: A Sustainable Approach

Li‐Na Guo, Hong-Jie Miao, Xin‐Hua Duan, Hongfei Liu, Yue-Jie Niu, Wenpeng Yang
article en
2 citations

Abstract

Sulfinamides make up a class of valuable chemicals with broad applications in organic synthesis and pharmaceutical research. Herein, we report a photocatalytic method for the straightforward synthesis of functionalized alkylsulfinamides from spiro pro-aromatic carbocycles with excellent atom economy. A variety of pro-aromatic carbocycles readily undergo C-C bond cleavage/sulfinamidation with <i>N</i>-sulfinylamines, yielding distally and site-specifically heteroarylated alkylsulfinamides with excellent yields and remarkable functional group tolerance. Mechanism studies indicate a radical pathway for this transformation.

The Journal of Organic ChemistryVol. 90(40)
State Key Laboratory of Applied Organic Chemistry, Lanzhou University (CN), Xi'an Jiaotong University (CN)
Openalex Percentile: Top 13%
Sulfur-Based Synthesis Techniques
1.87
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