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Access to β‐Lactam Sulfonamides from Sulfamoyl Chlorides via Photoredox Catalyzed C−S Bond Formation.

Authors :
Petek, Nejc
Brodnik, Helena
Grošelj, Uroš
Svete, Jurij
Štefane, Bogdan
Source :
Advanced Synthesis & Catalysis. 8/6/2024, Vol. 366 Issue 15, p3310-3315. 6p.
Publication Year :
2024

Abstract

Sulfonyl chlorides are a synthetically attractive source of sulfonyl radicals in photoredox catalysis and are useful precursors in the synthesis of sulfones. Sulfamoyl chlorides, on the other hand, remain poorly represented despite their similar potential. In this study, N‐chlorosulfonylated β‐lactams were prepared from readily available precursors and utilized in an atom transfer radical addition (ATRA) reaction with a variety of olefins, producing β‐lactam sulfonamides in 49–95% yields. β‐Lactams fused to a dihydro‐1,2‐thiazine ring which closely resemble carbacephems, a widely used class of antibiotics, were also synthesized by an intra‐molecular ATRA reaction. This methodology enables the preparation of β‐lactam sulfonamides, a class of compounds that are of great interest in pharmacology. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
16154150
Volume :
366
Issue :
15
Database :
Academic Search Index
Journal :
Advanced Synthesis & Catalysis
Publication Type :
Academic Journal
Accession number :
179110346
Full Text :
https://doi.org/10.1002/adsc.202400311