Issue 5, 2025

Electrochemical regioselective synthesis of sulfonyl 2,5-dihydrofuran-fused spiropyrimidines via multi-component radical cascade reactions

Abstract

In this work, we developed an efficient and environmentally friendly electrochemical three-component one-pot method for the generation of polysubstituted 2,5-dihydrofuran-fused spiropyrimidines containing valuable functional groups (–SO2R, –OR) that are difficult to access traditionally. In addition to water, various O-nucleophilic agents such as alcohols, carboxylates, and deuterium oxide can be seamlessly incorporated in one synthetic step. This protocol features a broad substrate scope (72 examples, up to 97% yield), excellent functional group compatibility, high regio- and diastereoselectivity, straightforward operation, and easy scalability, establishing it as a green and versatile method for constructing heterocycle-tethered spiropyrimidines. The mechanistic investigation reveals that the reaction proceeds via a cascade sulfonyl radical addition, 5-exo-trig ipso-cyclization, anodic oxidation, and subsequent nucleophilic attack process.

Graphical abstract: Electrochemical regioselective synthesis of sulfonyl 2,5-dihydrofuran-fused spiropyrimidines via multi-component radical cascade reactions

Supplementary files

Article information

Article type
Paper
Submitted
05 Nov 2024
Accepted
23 Dec 2024
First published
31 Dec 2024

Green Chem., 2025,27, 1499-1509

Electrochemical regioselective synthesis of sulfonyl 2,5-dihydrofuran-fused spiropyrimidines via multi-component radical cascade reactions

Q. Yang, R. Xu, C. Ni, X. Liu, Z. Qiao, Q. Zhang, D. Wang and H. Guo, Green Chem., 2025, 27, 1499 DOI: 10.1039/D4GC05637J

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