Study of the reactivity of carbamoyl fluorides as electrophiles in the synthesis of amides via Dual Ni/Photoredox catalysis

• Grant number: 24/08400-2
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: October 01, 2024
• Status: Discontinued
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Márcio Weber Paixão
• Grantee: Jennifer dos Santos Antunes
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

Transition metal catalysis is extremely recognized as an important tool in the construction of organic compounds. Recently, its combination with photoredox catalysis, culminating in the so-called metalaphotoredox double systems, has been extensively trained, leading to the development of dual catalytic systems capable of promoting a range of transformations inaccessible to both catalytic systems in isolation. Knowing that organic compounds containing amide moieties in their structures are widely disseminated in the pharmaceutical, agrochemical and materials industries, different research groups seek to develop new methodologies for synthesizing this class of compounds. Among the methodologies developed is the C-C coating of electrophilic carbamoyl equivalents with organic nucleophiles catalyzed by transition metals. In this sense, carbamoyl fluorides are good electrophilic components for these systems, since they are easy to obtain and present greater stability when compared to other carbamoyl electrophiles. Although carbamoyl fluorides have already been used in amide syntheses, reported methodologies consist of alkynylation or intramolecular recycling of these substrates. Even so, the development of radical approaches has not yet been reported. In this context, our research group proposes in this project the development of dual Ni/photoredox methodologies for the property of using carbamoyl fluorides as organic electrophiles.