Access to β-lactam sulfonamides from sulfamoyl chlorides via photoredox catalyzed C–S bond formation

Petek, Nejc (avtor), Brodnik, Helena (avtor), Grošelj, Uroš (avtor), Svete, Jurij (avtor), Štefane, Bogdan (avtor)

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.

• Jezik: Angleški jezik
• Ključne besede: β-lactams, photocatalysis, sulfonamides, sulfamoyl chlorides
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2024
• Št. strani: Str. 3310-3315
• Številčenje: Vol. 366, iss. 15
• PID: 20.500.12556/RUL-160180
• UDK: 547.7:544.526.5
• ISSN pri članku: 1615-4150
• DOI: 10.1002/adsc.202400311
• COBISS.SI-ID: 199399939
• Datum objave v RUL: 22.08.2024

Gradivo je del revije

• Naslov: Advanced synthesis & catalysis
• Založnik: Wiley
• ISSN: 1615-4150
• COBISS.SI-ID: 22726149

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: β-laktami, fotokataliza, sulfonamidi, sulfamoil kloridi

Projekti

• Financer: ARIS - Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije
• Številka projekta: P1-0179
• Naslov: Napredna organska sinteza in kataliza