TCT-DMSO/DMSO- <i>d</i> <sub>6</sub> Mediated a Mild Thioalkylation and Regioselective Intramolecular Cyclization Cascade to Access 3-Methylthiolated Indoles
A novel and facile method for the synthesis of methylthiolated indole derivatives is presented, relying on the activation of DMSO/DMSO-<i>d</i><sub>6</sub> by trichlorotriazine (TCT), which is the most cost-efficient, readily available, and stable reagent for DMSO activation to date. In addition, this process is proposed to involve an unprecedented DMSO stabilized methylsulfenium intermediate, derived from the TCT-DMSO/DMSO-<i>d</i><sub>6</sub> system, promoting metal-free, regioselective intramolecular cyclization.
Authors
- Haoyuan Fan (ORCID: https://orcid.org/0009-0005-2924-2948)
- P Xin (ORCID: https://orcid.org/0009-0009-2751-1816)
- Wei Wang
- Bo Feng (ORCID: https://orcid.org/0000-0001-5084-6715)
- Shixun Cao (ORCID: https://orcid.org/0000-0002-3915-2621)
- Yuexin Zhang (ORCID: https://orcid.org/0000-0001-7972-413X)
- Feng Hua (ORCID: https://orcid.org/0000-0002-8098-9095)
- Yong Zhang (ORCID: https://orcid.org/0000-0003-0397-7143)
- Linlin Xing (ORCID: https://orcid.org/0000-0002-7704-6942)
Institutions
- Peking University (CN)
- Center for Interdisciplinary Studies (IN)
- Anyang Institute of Technology (CN)
- Ministry of Education (BD)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-12-18
- DOI
- https://doi.org/10.1021/acs.joc.5c02451
- Citations
- 1
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.94