Organophotoredox Catalysis: Switchable Radical Generation from Alkyl Sodium Sulfinates for Sulfonylation and Alkylative Activation of C–C Bonds of Cyclopropenes

Generating alkyl radicals from the sulfonyl radicals remains challenging in synthetic chemistry. Here, we report an efficient photocatalyzed strategy using alkyl sodium sulfinates as both sulfonylating and alkylating reagents by controlling the reaction temperature. This methodology provides a versa...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-03, Vol.89 (6), p.3912-3925
Main Authors: Chandu, Palasetty, Biswas, Sourabh, Pal, Koustav, Sureshkumar, Devarajulu
Format: Article
Language:English
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Summary:Generating alkyl radicals from the sulfonyl radicals remains challenging in synthetic chemistry. Here, we report an efficient photocatalyzed strategy using alkyl sodium sulfinates as both sulfonylating and alkylating reagents by controlling the reaction temperature. This methodology provides a versatile protocol for synthesizing diastereoselective sulfonylated cyclopropanes and poly-substituted styrene derivatives. This methodology is successfully demonstrated with a wide variety of cyclopropenes and alkyl sulfinates, showcasing its broad substrate scope, high diastereo- and E/Z selectivity, and yielding good to excellent yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02743