Aerobic Visible‐Light Induced Intermolecular S−N Bond Construction: Synthesis of 1,2,4‐Thiadiazoles from Thioamides under Photosensitizer‐Free Conditions

Aerobic visible‐light induced intermolecular S−N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4‐thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides u...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-06, Vol.2021 (23), p.3398-3402
Main Authors: Zhuo, Liang, Xie, Shihua, Wang, Hui, Zhu, Hongjun
Format: Article
Language:English
Subjects:
1,2,4-Thiadiazole
Cyclization
Functional groups
Oxidation
Photocatalysis
Thiadiazoles
Thioamide
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Summary:Aerobic visible‐light induced intermolecular S−N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4‐thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single‐electron‐transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4‐thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S−N bonds. A green approach for S−N construction with concomitant synthesis of1,2,4‐thiadiazoles was developed by visible‐light induced oxidative cyclization of thioamides under photosensitizer‐free conditions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100440