O <sub>2</sub> -Controlled Acid-Mediated Sulfenylation/Cyclization of Tethered Malononitriles and Sulfides toward Divergent Synthesis of Mono/Dithio-cyclopentenones
We have described an efficient, O<sub>2</sub>-controlled acid-mediated reaction that enables divergent synthesis of mono- and dithio-cyclopentenones from tethered malononitriles and sulfides. Monosulfenylated products are obtained directly with HCl in good to excellent yields, whereas the additional use of O<sub>2</sub> as the oxidant and a one-pot two-step operation favors the formation of disulfenylated analogs. This method features a broad substrate scope, excellent regioselectivities, mild conditions, and green oxidant. Gram-scale synthesis and product diversification demonstrate the practical utility of this protocol.
Authors
- Wen Xiong (ORCID: https://orcid.org/0000-0002-9228-9440)
- Linjing Wu (ORCID: https://orcid.org/0000-0003-0320-2508)
- Sha Wu (ORCID: https://orcid.org/0000-0003-2802-7806)
- Ting Xiao (ORCID: https://orcid.org/0000-0001-5578-1228)
- Tao Ling (ORCID: https://orcid.org/0000-0002-7993-0328)
- Huili Li
- Fei Jiang
- Xiangchun Shen
- Dandan He
Institutions
- Guiyang Medical University (CN)
- Institute of Medicinal Plant Development (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-01-15
- DOI
- https://doi.org/10.1021/acs.orglett.5c04770
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00