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Electrochemical Regioselective C(sp 2 )–H Bond Chalcogenation of Pyrazolo[1,5- a ]pyrimidines via Radical Cross-Coupling at Room Temperature

Year: 2024

Type: article

Abstract: Herein, we disclose an electrochemical approach for the C(sp 2 )–H chalcogenation of pyrazolo[1,5- a ]pyrimidines. This technique offers an oxidant and catalyst-free protocol for achieving regioselective chalcogenation of pyrazolo[1,5- a ]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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c00856

Authors: Abhinay S. Chillal, Rajesh T. Bhawale, Siddharth Sharma, Umesh A. Kshirsagar

Institutions: Indian Institute of Technology Indore, Mohanlal Sukhadia University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Council of Scientific and Industrial Research, India, Indian Institute of Technology Indore, Science and Engineering Research Board

Awards: G4132406576, G6242202959