TMSCl-Promoted Sulfonylation of Propargylic Alcohols with Sodium Sulfinates for the Construction of (<i>E</i>)-1,3-Disulfonylpropenes and (<i>E</i>)-1-Sulfonylpropenols
A direct and novel transformation of propargylic alcohols with sodium sulfinates for the regio- and stereoselective synthesis of (<i>E</i>)-1,3-disulfonylpropenes and (<i>E</i>)-1-sulfonylpropenols was successfully developed in the presence of TMSCl under mild conditions. The preliminary mechanistic experiments demonstrated that the reaction underwent an unprecedented dual nucleophilic substitution/radical addition process, in which sodium sulfinates were used not only as nucleophiles but also as a sulfonyl radical source.
Authors
- Qiang Xiao (ORCID: https://orcid.org/0000-0003-2812-7778)
- Shimin Jiang
- Mu‐Jia Luo (ORCID: https://orcid.org/0000-0001-5827-749X)
- Ruchun Yang
- Haiyang Huang (ORCID: https://orcid.org/0000-0002-5520-0945)
- Haixin Ding (ORCID: https://orcid.org/0000-0003-1569-7333)
- Xi Chen (ORCID: https://orcid.org/0000-0001-7303-148X)
- Meng Liang
- Xian‐Rong Song (ORCID: https://orcid.org/0000-0002-8547-7881)
Institutions
- Jiangxi Science and Technology Normal University (CN)
- Institute of Organic Chemistry (HU)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-12
- DOI
- https://doi.org/10.1021/acs.joc.4c01829
- Citations
- 5
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangxi Province
- Jiangxi Science and Technology Normal University