PCCP‐Catalyzed Synthesis of Tetrasubstituted Allenes Bearing Heteroaromatic Sulfenyl Group

We report a Brønsted acid‐catalyzed synthesis of tetrasubstituted allenyl compounds decorated with heterocyclic sulfenyl group. The reaction proceeds readily from available propargylic alcohols in the presence of pentacarboxycyclopenatadienes (PCCPs) as organocatalysts. The developed strategy provid...

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Bibliographic Details
Published in:European journal of organic chemistry 2023-08, Vol.26 (32), p.n/a
Main Authors: Kamlar, Martin, Císařová, Ivana, Veselý, Jan
Format: Article
Language:English
Subjects:
Alcohols
Allene
Brønsted acid
Chemical synthesis
cyclopentadiene
organocatalysis
propargylic alcohol
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Summary:We report a Brønsted acid‐catalyzed synthesis of tetrasubstituted allenyl compounds decorated with heterocyclic sulfenyl group. The reaction proceeds readily from available propargylic alcohols in the presence of pentacarboxycyclopenatadienes (PCCPs) as organocatalysts. The developed strategy provides tetrasubstituted allene derivatives in high yields (from 55 to 98 %) and under mild reaction conditions. Simple, one‐step Brønsted acid catalyzed reaction of propargyl alcohol derivatives with heterocyclic thiols was performed with the aid of pentacarboxycyclopenatadiene (PCCP) catalyst. This reported approach provides an access to tetrasubstituted allenes substituted with heterocyclic thioethers in good to excellent yield under mild reaction conditions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202300400