Alkyl Sulfinate Anion-Mediated Hydrosulfonylation of Alkenes/Alkynes via SO<sub>2</sub> Insertion: Access to Alkyl Sulfones
An alkyl sulfinate anion-mediated hydrosulfonylation of alkenes/alkynes with alkyl bromides involving SO<sub>2</sub> insertion has been developed for the synthesis of alkyl sulfones. Sodium dithionite (Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub>) acts as both an SO<sub>2</sub> surrogate and a single-electron donor, thereby obviating the need for metal catalysts or metallic reductants. This protocol features broad substrate scope and high functional group tolerance, accommodating a range of bioactive scaffold molecules such as citronellol, estrone, borneol, and cholesterol. Mechanistic investigations reveal that the alkyl sulfinate anion is a key intermediate, and deuterium-labeling experiments confirm that trace H<sub>2</sub>O in the solvent serves as the proton source in the protonation step.
Authors
- Jinhua Zhou (ORCID: https://orcid.org/0000-0002-1163-002X)
- Hongbo Xiao (ORCID: https://orcid.org/0000-0002-4138-371X)
- Li‐Jun Wu (ORCID: https://orcid.org/0000-0002-2067-6732)
- Dazhi Sun (ORCID: https://orcid.org/0000-0001-7553-3141)
- Lin Wang (ORCID: https://orcid.org/0000-0003-4032-7916)
- Qing Li (ORCID: https://orcid.org/0000-0003-4807-030X)
- Shaofeng Pi (ORCID: https://orcid.org/0000-0003-0277-7254)
- Ying Man
- Shuang-Feng Yin
Institutions
- Central South University of Forestry and Technology (CN)
- Hunan Institute of Engineering (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-04
- DOI
- https://doi.org/10.1021/acs.orglett.5c02678
- Citations
- 2
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Natural Science Foundation of Hunan Province
- Scientific Research Foundation of Hunan Provincial Education Department