Synthesis of (Hetero)Arylsulfonamides via photocatalytic C-H-sulfamoylation using sulfamoyl radicals

• Grant number: 22/08837-6
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• Start date: January 10, 2023
• End date: January 09, 2024
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Giuliano Cesar Clososki
• Grantee: Thais Rodrigues Arroio
• Supervisor: Georg Manolikakes
• Host Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
• Institution abroad: University of Kaiserslautern, Germany
• Associated to the scholarship: 20/13962-9 - Synthetic studies aiming at the preparation of new pyridoindois of medicinal interest, BP.DR

Abstract

Sulfonamides compounds represent and important class of compounds due to their wide range of biological and pharmaceutical applications, including in the first generation of antibiotics. Despite their recognized importance, several classical methodologies to synthesize sulfonamides derivatives have limitations regarding the sustainability aspect, which is an increasingly concern for economy and society. With the resurgence of photochemistry as a viable and advantageous approach for the synthesis of novel compounds as well as with modern C-H functionalization methodologies, it is possible to address such concerns and achieve more sustainable, safe and efficient ways to obtain value-added organic compounds. The combination of these two approaches for the development of novel sulfonamides compounds offers an interesting research opportunity to sustainable synthetic methods. Thus, this research proposal aims at the development of a direct photocatalyzed C-H sulfamoylation methodology for the synthesis of potentially bioactive (hetero)arylsulfonamides using sulfamoyl radicals as reaction intermediates. Although the addition of these radical species has been described to double carbon bonds, there is no precedent in the literature for the proposed C-H functionalization. Its worth mentioning that the development of the present proposal in the Manolikakes Group will complement the current PhD studies in Brazil that are focused on the preparation of new bioactive heterocycles using different synthetic approaches. (AU)