Photoinduced Vicinal Sulfamoyloximation of Alkenes: Harnessing Bifunctional Nitrosamines via a Rapid Radical Trapping Strategy.

Org Lett

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China.

Published: July 2024

We developed a photoinduced method for vicinal sulfamoyloximation of alkenes using -nitrosamines as bifunctional reagents, with DABSO serving as both a sulfonyl source and a rapid aminyl radical trap. This strategy prevents radical recombination, enabling bifunctional activation under neutral conditions to generate key sulfamoyl radicals. It accommodates broad substrate scope and functional group compatibility, enabling late-stage modifications of bioactive molecules and expanding sulfonamide diversity in organic synthesis.

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http://dx.doi.org/10.1021/acs.orglett.4c02245DOI Listing

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