An aryl thiol-vinyl azide coupling reaction and a thiol-vinyl azide coupling/cyclization cascade: efficient synthesis of β-ketosulfides and arene-fused 5-methylene-2-pyrrolidinone derivatives

The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide. A thiol-vinyl azide coupling/cyclization cas...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-06, Vol.19 (23), p.5169-5176
Main Authors: Wang, Yong, Wang, Yu-Jiao, Liang, Xian-Chen, Shen, Mei-Hua, Xu, Hua-Dong, Xu, Defeng
Format: Article
Language:English
Subjects:
Aromatic compounds
Azide
Coupling
NMR
Nuclear magnetic resonance
Substitutes
Thiols
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Summary:The addition reaction of thiol to vinyl azide has been extensively studied. Variously substituted aryl thiols are all viable for this coupling process. The scope of the other partner is successfully expanded from α-aryl vinyl azide to α-alkyl vinyl azide. A thiol-vinyl azide coupling/cyclization cascade is realized with substituted aryl vinyl azides carrying a 2-methoxycarbonyl group. The value of β-ketosulfide products was demonstrated by its application in S-heterocycle synthesis. A radical addition-fragmentation intermediate of vinyl azide can be intercepted by a neighbouring ester group. β-Ketosulfides could be a convenient platform for S-heterocycle synthesis.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00328c