Brønsted Acid Promoted Sulfenylacyloxylation of Alkynes: Access to 4‐Sulfenylisocoumarins

Presented herein is the Brønsted acid (MsOH) mediated electrophilic sulfenylacyloxylation of o‐alkynylbenzoates via alkyne activation by in‐situ formed sulfonium cations from bench‐stable N‐thioaryl/alkyl‐succinimides followed by the intramolecular regioselective cyclization. The transformation prov...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 364; no. 20; pp. 3496 - 3500
Main Authors Saha, Arijit, Ramesh, E., Sahoo, Akhila K.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.10.2022
Wiley Subscription Services, Inc
Subjects
4-Sulfenylisocoumarin
Alkynes
Chemistry
Chemistry, Applied
Chemistry, Organic
Electrophilic cyclization
Functional groups
Late-stage functionalization
Metal-free
Methanesulfonic acid
Phthalimides
Physical Sciences
Science & Technology
Succinimides
Metal-free
ANNULATION
4-Sulfenylisocoumarin
HYDRANGEAE DULCIS FOLIUM
EFFICIENT SYNTHESIS
Methanesulfonic acid
FACILE SYNTHESIS
Late-stage functionalization
Electrophilic cyclization
ALPHA-PYRONES
SELECTIVE SYNTHESIS
MULTICOMPONENT SYNTHESIS
ISOCOUMARINS
DERIVATIVES
CYCLIZATION
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Summary:Presented herein is the Brønsted acid (MsOH) mediated electrophilic sulfenylacyloxylation of o‐alkynylbenzoates via alkyne activation by in‐situ formed sulfonium cations from bench‐stable N‐thioaryl/alkyl‐succinimides followed by the intramolecular regioselective cyclization. The transformation provides access to structurally diverse 4‐sulfenylisocoumarins in 77–98% yields with broad functional group compatibility. The reaction scalability and reusability of phthalimide protecting group make this protocol synthetically viable.
Bibliography:These authors are contributed equally at this work.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200761