Electrochemical Regioselective C(sp <sup>2</sup> )–H Bond Chalcogenation of Pyrazolo[1,5- <i>a</i> ]pyrimidines via Radical Cross-Coupling at Room Temperature
Herein, we disclose an electrochemical approach for the C(sp<sup>2</sup>)-H chalcogenation of pyrazolo[1,5-<i>a</i>]pyrimidines. This technique offers an oxidant and catalyst-free protocol for achieving regioselective chalcogenation of pyrazolo[1,5-<i>a</i>]pyrimidines. The procedure uses only 0.5 equiv. of diaryl chalcogenides which underscores the atom economy of the protocol. Key attributes of this methodology include mild reaction conditions, short reaction time, utilization of cheap electrode materials, and eco-friendly reaction conditions. Cyclic voltammetry studies and radical quenching experiments revealed a radical cross-coupling pathway for the reaction mechanism.
Authors
- Siddharth Sharma (ORCID: https://orcid.org/0000-0003-2759-4155)
- Abhinay S. Chillal
- Rajesh T. Bhawale (ORCID: https://orcid.org/0000-0001-5611-5294)
- Umesh A. Kshirsagar (ORCID: https://orcid.org/0000-0002-3224-7281)
Institutions
- Mohanlal Sukhadia University (IN)
- Indian Institute of Technology Indore (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-09-16
- DOI
- https://doi.org/10.1021/acs.joc.4c00856
- Citations
- 16
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 4.00
Funders
- Council of Scientific and Industrial Research, India
- Indian Institute of Technology Indore
- Science and Engineering Research Board