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March 27, 2026The Journal of Organic Chemistry2 citations

Copper-Mediated Sulfimidations of Benzylic C(sp 3 )–H Bonds

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GHGuoling HuangZZZhibo ZhaoZHZhiliang Huang

Key Points

  • The aim is to develop a copper-mediated method for activating benzylic C(sp3)–H bonds to form C–S bonds.
  • Utilized copper as a catalyst under oxidative conditions.
  • Employed readily available methylarenes as substrates.
  • Explored reactions to produce benzylic sulfilimines from C(sp3)–H precursors.
  • Investigated a range of sulfenamides for compatibility.
  • Achieved moderate yields of benzylic sulfilimines.
  • Demonstrated broad applicability to various methylarenes.
  • Provided a complementary route to existing synthetic methods.

Abstract

In this study, we describe a strategy for benzylic C(sp3)–H activation that enables C–S bond formation through a copper-mediated sulfimidation. Leveraging readily available methylarenes under oxidative conditions, the method provides a complementary route to benzylic sulfilimines directly from simple C(sp3)–H precursors. It is applicable to a representative range of sulfenamides and methylarenes, amenable to scale-up, and typically delivers benzylic sulfilimines in moderate yields.

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Cite This Study

Huang et al. (2026) studied this question.

synapsesocial.com/papers/69c6202f15a0a509bde188f4https://doi.org/10.1021/acs.joc.5c02965
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Also Consider

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  1. 1Synthesis of Cyclic Sulfilimines and Sulfoximines via Copper‐Mediated C(sp<sup>2</sup>)–H Sulfanylation of Benzylamines with a Catalytic Transient Directing Group2025 · 2 citations
  2. 2Copper-Catalyzed Asymmetric C–H Sulfilimination of Arenes via HAT-Primed C–S Radical–Radical Coupling2025 · 30 citations
  3. 3Photoinduced Copper‐Catalyzed <i>para</i> ‐Selective C–H <i>S</i> ‐Arylation of Benzylic Oxime Carbonates with Sulfenamides2026
  4. 4Enantioselective Synthesis of Sulfilimines Enabled by Photoinduced Copper-Catalyzed C(sp <sup>3</sup> )-H Sulfimidation2026 · 3 citations
  5. 5Enantioselective Alkyl C−H Sulfimidation Enabled by Copper Catalysis2025