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

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

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.

• Language: English
• Keywords: β-lactams, photocatalysis, sulfonamides, sulfamoyl chlorides
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2024
• Number of pages: Str. 3310-3315
• Numbering: Vol. 366, iss. 15
• PID: 20.500.12556/RUL-160180
• UDC: 547.7:544.526.5
• ISSN on article: 1615-4150
• DOI: 10.1002/adsc.202400311
• COBISS.SI-ID: 199399939
• Publication date in RUL: 22.08.2024

Record is a part of a journal

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

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: β-laktami, fotokataliza, sulfonamidi, sulfamoil kloridi

Projects

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: P1-0179
• Name: Napredna organska sinteza in kataliza