Metal Free Benzylation and Alkylation of Quinoxalin‐2(1H)‐ones with Alkenes Triggered by Sulfonyl Radical Generated from Sulfinic Acids

A metal‐free domino multicomponent reaction for the direct C−H benzylation and alkylation of quinoxalin‐2(1H)‐ones using alkenes is described. Triggered by the sulfonyl radical generated from sulfinic acid, the alkenes are transformed to alkyl radicals that react exclusively at the C‐3 position of q...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-12, Vol.361 (24), p.5534-5539
Main Authors: Sekhar Dutta, Himangsu, Ahmad, Ashfaq, Khan, Afsar Ali, Kumar, Mohit, Raziullah, Koley, Dipankar
Format: Article
Language:English
Subjects:
Alkenes
Alkylation
benzylation
quinoxalin-2(1H)-one
radical cascade
Sulfones
sulfonylation
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Summary:A metal‐free domino multicomponent reaction for the direct C−H benzylation and alkylation of quinoxalin‐2(1H)‐ones using alkenes is described. Triggered by the sulfonyl radical generated from sulfinic acid, the alkenes are transformed to alkyl radicals that react exclusively at the C‐3 position of quinoxalin‐2(1H)‐ones. Importantly, the method not only functionalizes medicinally important quinoxalin‐2(1H)‐one scaffold, but also furnishes diverse medicinally relevant sulfones in good to excellent yields under mild conditions.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901212