Advanced Synthesis and Catalysis
Nejc Petek, Helena Brodnik, Uroš Grošelj, Jurij Svete, and Bogdan Štefane
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 precursorsand 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 ringwhich 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.
Read article: Adv. Synth. Catal., 2024, 366, 3310
