Copper-catalyzed thiolation of imidazo[1,2-a]pyridines with (hetero)aryl thiols using molecular oxygen

A new and facile copper-catalyzed thiolation of imidazo[1,2-a]pyridines with (hetero)aryl thiols was developed for the formation of C–S bond by using molecular oxygen as oxidant under base-free conditions. The presented protocol has provided the selective C-3 sulfenated products with good yield. A c...

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Bibliographic Details
Published inCatalysis communications Vol. 66; pp. 83 - 86
Main Authors Zheng, Zhishuo, Qi, Deyu, Shi, Lei
Format Journal Article
LanguageEnglish
Published Elsevier B.V 05.06.2015
Subjects
(Hetero)aryl thiols
Copper-catalyzed
Imidazo[1,2-a]pyridines
Molecular oxygen
Thiolation
Imidazo[1,2-a]pyridines
Molecular oxygen
Copper-catalyzed
(Hetero)aryl thiols
Thiolation
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Summary:A new and facile copper-catalyzed thiolation of imidazo[1,2-a]pyridines with (hetero)aryl thiols was developed for the formation of C–S bond by using molecular oxygen as oxidant under base-free conditions. The presented protocol has provided the selective C-3 sulfenated products with good yield. A computational study was carried out by using the B3LYP density functional theory to elucidate the regioselectivity of C-2 and C-3. Calculation results indicated that the thiolation toward C-3 was easier and smoother, which was consistent with our experiment results. •Cu-catalyzed cross-coupling of imidazo[1,2-a]pyridines with thiols•The selective C-3 sulfenated products were formed using molecular oxygen as oxidant.•An efficient method for the formation of C–S bond to synthize imidazo[1,2-a]pyridines
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2015.03.023