Aryne triggered [2,3]-sigmatropic rearrangement of allyl and propargyl thioethers

An efficient protocol for [2,3]-sigmatropic rearrangement of allyl and propargyl thioethers is reported. The key sulfonium ylide intermediate is in situ formed via S-arylation of arynes. This transition metal-free method allows for ready access to a wide array of functionalized thioether derivatives...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 15; no. 23; pp. 4946 - 4950
Main Authors Tan, Jiajing, Zheng, Tianyu, Xu, Kun, Liu, Changyao
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SULFUR YLIDES
CYCLOADDITION
AMINATION
FACILE ACCESS
AMINES
EMPLOYING ARYNES
ARYLATION
GENERATION
SULFONIUM YLIDES
TERTIARY
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Summary:An efficient protocol for [2,3]-sigmatropic rearrangement of allyl and propargyl thioethers is reported. The key sulfonium ylide intermediate is in situ formed via S-arylation of arynes. This transition metal-free method allows for ready access to a wide array of functionalized thioether derivatives in good to excellent yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00914c