Synthesis of Sulfenylated Isocoumarins/Pyrones Mediated by Sulfoxide-Stabilized Sulfenium Electrophiles Derived from TCT-Sulfoxide
The facile synthesis of methylthiolated and <i>d</i><sub>3</sub>-methylthiolated isocoumarins and pyrones mediated by DMSO/DMSO-<i>d</i><sub>6</sub>-stabilized methylsulfenium cation electrophiles derived from the TCT-DMSO/DMSO-<i>d</i><sub>6</sub> system via the interrupted Pummerer reaction has been developed. Herein, readily available trichlorotriazine (TCT), which is the most cost-efficient reagent for DMSO activation, was employed in an amount of 40 mol % relative to the substrate. Additionally, the sulfur sources were not confined to DMSO or DMSO-<i>d</i><sub>6</sub> alone, and both diethyl sulfoxide and phenyl methyl sulfoxide were also compatible, allowing the installation of methylthio, <i>d</i><sub>3</sub>-methylthio, ethylthio, and phenylthio groups on the cyclization products.
Authors
- Haoyuan Fan (ORCID: https://orcid.org/0009-0005-2924-2948)
- Ning Han (ORCID: https://orcid.org/0000-0003-0920-9049)
- Lei Xing (ORCID: https://orcid.org/0000-0003-2536-5359)
- Shixun Cao (ORCID: https://orcid.org/0000-0002-3915-2621)
- Yong Zhang
- Hezhuang Feng
- Kai Wang
- Zhenyan Yang
Institutions
- Peking University (CN)
- Center for Interdisciplinary Studies (IN)
- Shijiazhuang Yiling Pharmaceutical (China) (CN)
- Anyang Institute of Technology (CN)
- Ministry of Education (BD)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-03-17
- DOI
- https://doi.org/10.1021/acs.joc.5c03171
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00