γ-Ketosulfones are crucial building blocks in medicinal chemistry, serving as key bioactive components in antibacterial, anticoagulant, and antitumor drugs. However, traditional synthesis methods typically involve:

• Oxidation of γ-ketothioethers: Requires strong oxidants and harsh conditions.
• Derivatization of sulfinates: Involves cumbersome, multi-step processes.

These limitations hinder broader applications, making it difficult to achieve efficient, scalable production.

A Breakthrough in γ-Ketosulfone Synthesis

Professor Lian Zhong from Sichuan University and his team developed an innovative method for synthesizing γ-ketosulfone compounds using:

• Cyclopropanol and aryldiazotetrafluoroborate as starting materials.
• SOgen, a next-generation exogenous SO₂ replacement reagent.

This approach offers:

• High yields under mild conditions
• Low catalyst loading
• Excellent functional group tolerance
• Simple and direct access to structurally diverse γ-ketosulfones

By leveraging the Skrydstrup two-chamber system, SOgen can fully release SO₂ within 5 minutes, avoiding the interference of byproducts in the main reaction system.

Figure 1 Synthesis of γ-ketosulfone compounds by sulfur dioxide insertion method[1]

Advantages of SOgen in Organic Synthesis

J&K Scientific exclusively supplies the SOgen reagent, developed by Professor Lian Zhong’s research group. Its key advantages include:

• Fast and Complete SO₂ Release:
  Achieves full release within 5 minutes, ensuring rapid reaction times.

• Main Reaction Integrity:
  Prevents organic byproducts from interfering with the desired synthesis pathway.

• Stability and Ease of Storage:
  SOgen is stable under standard conditions and easy to handle, unlike many traditional SO₂-releasing reagents.

• Cost-Effectiveness and Versatility:
  Offers a cheaper, more controllable alternative, suitable for a wide range of applications in medicinal and materials chemistry.

Example Reaction:
Place SOgen in the reactor, add an equivalent of p-toluene, and use tetradecane as the solvent (1.0 mL/0.2 mmol SOgen). Seal and heat at 100°C for 10 minutes. The reaction concludes when the solution becomes clear, signaling complete SO₂ release and product formation.

How to use

Figure 2 How to use SOgen reagent

About Professor Lian Zhong

Professor Lian Zhong is a leading scientist at the National Key Laboratory of Biotherapy/Dermatology, West China Hospital, Sichuan University. His research focuses on:

• Sulfur dioxide resource utilization
• Mechanochemistry
• Design and synthesis of small-molecule targeted drugs

He has led multiple national and provincial research projects and published extensively in top-tier journals, including:

• Science
• Nature Communications
• Angewandte Chemie International Edition
• ACS Catalysis

He was selected for the National Overseas High-level Young Talent Project (Youth Thousand Talents) and serves as an editorial board member for the European Journal of Organic Chemistry.

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References

1. Shen L, Zhang X, Lian Z. Copper-catalyzed ring-opening sulfonylation of cyclopropanols via the insertion of sulfur dioxide toward the synthesis of γ-keto aryl sulfones[J]. Organic Chemistry Frontiers, 2023, 10(13): 3239-3244.