Issue 8, 2024

Visible-light-driven three-component annulation for the synthesis of highly functionalized 2-iminothiazolidin-4-ones without photocatalysts

Abstract

We have developed a photocatalyst/base/metal-free, visible-light-driven three-component annulation protocol to access fully substituted 2-iminothiazolidin-4-one derivatives from isothiocyanates, amines, and aryl diazoacetates using a low-energy white light source at room temperature in open air. The [2 + 2 + 1] reaction undergoes successive C–N/C–S bond formation in one pot. This transformation proceeds under extremely mild conditions with a good yield and a good functional group tolerance. Mechanistic studies showed that the reaction involves the formation of free carbene intermediates from aryl diazoacetates under visible light irradiation.

Graphical abstract: Visible-light-driven three-component annulation for the synthesis of highly functionalized 2-iminothiazolidin-4-ones without photocatalysts

Supplementary files

Article information

Article type
Communication
Submitted
23 Jan 2024
Accepted
20 Mar 2024
First published
22 Mar 2024

Green Chem., 2024,26, 4477-4483

Visible-light-driven three-component annulation for the synthesis of highly functionalized 2-iminothiazolidin-4-ones without photocatalysts

B. Yang, Y. Wang, X. Yang, Y. Li, Z. Zhang, X. Hua, L. Ouyang, L. Zheng and W. Guo, Green Chem., 2024, 26, 4477 DOI: 10.1039/D4GC00375F

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