Trichloroacetonitrile-Mediated Oxidation of Sulfides and Benzylic C–H Bonds via Photoexcited Radical Reactions under Clean Conditions
The protocol using only trichloroacetonitrile (CCl<sub>3</sub>CN) or CCl<sub>3</sub>CN/methanol to achieve oxidation of sulfides and benzylic C-H bonds in open air was established. Highly selective oxidation of sulfides to sulfoxides and efficient oxidation of benzylic C-H bonds were realized under clean and mild conditions, respectively. The main features of this protocol are a wide substrate scope, high yields, gram-scale preparation, and efficient conversion of various pharmaceutical molecules. The reactions were performed in air under light irradiation, and the mechanism was demonstrated to involve a radical process. This protocol provides a sustainable and straightforward method for the oxidation of sulfides and benzylic C-H bonds.
Authors
- Shuaikun Liu
- Lizhen Fang (ORCID: https://orcid.org/0000-0001-8594-4710)
- Yingchang Guo
- Xinqiang Tan (ORCID: https://orcid.org/0000-0003-2200-9340)
- Yi Liu (ORCID: https://orcid.org/0000-0003-0548-6073)
- Jialiang Zhang (ORCID: https://orcid.org/0000-0002-7421-8024)
- Kunyi Zhang (ORCID: https://orcid.org/0009-0007-8769-6870)
Institutions
- First Affiliated Hospital of Xinxiang Medical University (CN)
- Henan Medical University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-27
- DOI
- https://doi.org/10.1021/acs.orglett.5c01339
- Citations
- 5
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 4.68