Photoredox/Copper-Cocatalyzed Domino Annulation of Oxime Esters and NH<sub>4</sub>SCN: Access to Fully Substituted 2-Aminothiazoles

Domino cyclization of oxime esters and NH<sub>4</sub>SCN facilitated by photoredox and copper cocatalysis has been established. Various structurally diverse fully substituted 2-aminothiazoles have been obtained in good yields at room temperature. It is featured by mild conditions, favorable functional group tolerance, and wide substrate scope. The present reaction is amenable to gram-scale synthesis, which is expected to find potential applications in organic synthesis and drug discovery. A plausible reaction mechanism is proposed.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-10-07
DOI
https://doi.org/10.1021/acs.joc.4c01951
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.50

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article

Photoredox/Copper-Cocatalyzed Domino Annulation of Oxime Esters and NH4SCN: Access to Fully Substituted 2-Aminothiazoles

Shujun Cao, Yichao Wan, Yong-Yan Luo, Yanyan Zhang et al.
2 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
0.50
article

Photoredox/Copper-Cocatalyzed Domino Annulation of Oxime Esters and NH4SCN: Access to Fully Substituted 2-Aminothiazoles

Shujun Cao, Yichao Wan, Yong-Yan Luo, Yanyan Zhang, Mengting Liu, Xiaozhen Wang
article en
2 citations

Abstract

Domino cyclization of oxime esters and NH<sub>4</sub>SCN facilitated by photoredox and copper cocatalysis has been established. Various structurally diverse fully substituted 2-aminothiazoles have been obtained in good yields at room temperature. It is featured by mild conditions, favorable functional group tolerance, and wide substrate scope. The present reaction is amenable to gram-scale synthesis, which is expected to find potential applications in organic synthesis and drug discovery. A plausible reaction mechanism is proposed.

The Journal of Organic ChemistryVol. 89(20)
Hunan University of Science and Technology (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hunan Province, Science and Technology Program of Hunan Province
Openalex Percentile: Top 39%
Radical Photochemical Reactions
0.50
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