Silver-Catalyzed 1,2-Thiosulfonylation of Alkenes: Development of a Nucleophilic <i>d</i><sub>3</sub>-Methylthiolating Reagent
Development of robust <i>d</i><sub>3</sub>-methylthiolating reagents represents an attractive synthetic method to access deuterated molecules in the field of drug discovery. Here, we report a straightforward strategy to prepare electrophilic <i>S</i>-methyl-<i>d</i><sub>3</sub> arylsulfonothioates in one-step without column purification. These reagents exhibit good radical reactivity toward silver-catalyzed vicinal thiosulfonylation of alkenes or 1,6-enynes on water. As a result, simultaneous incorporation of both SCD<sub>3</sub> and ArSO<sub>2</sub> units into unsaturated carbon-carbon bonds with 100% atom economy has been established. Moreover, the ATRA adducts with >99% D incorporation can serve as nucleophilic <i>d</i><sub>3</sub>-methylthiolating synthons via retro-Michael addition under mild basic conditions, providing a good alternative in trideuteromethylthiolating alkyl iodides to access corresponding trideuteromethyl sulfides with high efficiency.
Authors
- Xinxin Shao (ORCID: https://orcid.org/0000-0001-5526-8344)
- Yan Zhang (ORCID: https://orcid.org/0000-0001-8554-4098)
- Jirong Wu
- Guofang Guo
- Zhiyong Ye
Institutions
- Hangzhou Normal University (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-09-26
- DOI
- https://doi.org/10.1021/acs.joc.4c01787
- Citations
- 4
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- National Natural Science Foundation of China
- Hangzhou Science and Technology Bureau
- Natural Science Foundation of Zhejiang Province