Visible-light-induced intramolecular C-S bond formation for practical synthesis of 2,5-disubstituted 1,3,4-thiadiazoles

A general and facile visible-light mediated protocol for the synthesis of 2-arylamino-5-aryl-1,3,4- thiadiazoles via one-pot condensation and intramolecular C-S coupling cascade reaction has been developed. This protocol is mild, practical, metal-free and exogenous oxidant-free, and only involves Eo...

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Bibliographic Details
Published inSynthetic communications Vol. 53; no. 1; pp. 40 - 48
Main Authors Shi, Zhaocheng, Li, Ruohan, Lan, Wenqing, Wei, Haishan, Sheng, Shouri, Chen, Junmin
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 02.01.2023
Taylor & Francis Ltd
Subjects
1,3,4-thiadiazole
Cascade chemical reactions
Chemistry
Chemistry, Organic
Functional groups
intramolecular C-S bond formation
Metal-free
Oxidizing agents
photoredox catalysis
Physical Sciences
Science & Technology
Substrates
Synthesis
Thiadiazoles
visible light
1
Metal-free
3
ANTICANCER
intramolecular C-S bond formation
4-thiadiazole
ANTICONVULSANT
CONDENSATION
visible light
photoredox catalysis
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Summary:A general and facile visible-light mediated protocol for the synthesis of 2-arylamino-5-aryl-1,3,4- thiadiazoles via one-pot condensation and intramolecular C-S coupling cascade reaction has been developed. This protocol is mild, practical, metal-free and exogenous oxidant-free, and only involves Eosin Y as photocatalyst using oxygen as the sole terminal oxidant. This protocol exhibits synthetic simplicity, broad scope of substrates, and excellent functional group compatibility. Gram-scale synthesis can be also facilitated with a satisfactory yield, which opens up the possibility of practical applications.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2022.2149342