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September 28, 2025The Journal of Organic Chemistry5 citations

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

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WYWenpeng YangHLHongfei LiuHMHong-Jie Miao

Key Points

  • The method yields functionalized alkylsulfinamides with excellent atom economy, indicating its efficiency.
  • Mechanism studies reveal a radical pathway, suggesting a novel reaction mechanism for synthesis.
  • This approach circumvents traditional limitations in organic synthesis by utilizing pro-aromatic carbocycles effectively.
  • The resulting alkylsulfinamides exhibit remarkable functional group tolerance, expanding their potential applications.

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 N-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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Cite This Study

Yang et al. (2025) studied this question.

synapsesocial.com/papers/68d909fc41e1c178a14f5bb9https://doi.org/10.1021/acs.joc.5c01834
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Also Consider

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  1. 1Iron-Catalyzed Photochemical Synthesis of Sulfinamides from Aliphatic Hydrocarbons and Sulfinylamines2024 · 35 citations
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  3. 3Construction of C–S and C–Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones2025 · 16 citations
  4. 4Photoredox‐Catalyzed Deconstructive Thiolation and Selenylation of Pro‐Aromatic Carbocycles2025 · 5 citations
  5. 5Dual-nickel/photoredox-catalyzed acylation of spiro-dihydroquinazolinones with carboxylic acids via an aromatization-driven deconstructive strategy2025 · 14 citations