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Abstract
This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.
Highlights
N-Arylacetamides constitute the core of many structural motifs found in biologically active compounds, drugs, and agrochemicals.[1]
Common approaches for the synthesis of N-arylacetamides involve the aminolysis of activated carboxylic acid derivatives, such as halides, anhydrides, azides, or activated esters, which are mostly generated in an extra step using hazardous, expensive or waste-intensive reagents.[4]
Catalytic methods have recently been developed to access N-arylacetamides.4b,5 Pioneering work in this eld was reported by Goldberg[6] in the copper catalyzed synthesis of N-arylamide from amide through a C–N coupling process, albeit under harsh conditions limiting its broad application in organic synthesis
Summary
N-Arylacetamides constitute the core of many structural motifs found in biologically active compounds, drugs (e.g., lidocaine, atorvastatin), and agrochemicals (e.g., boscalid).[1]. Catalytic methods have recently been developed to access N-arylacetamides.4b,5 Pioneering work in this eld was reported by Goldberg[6] in the copper catalyzed synthesis of N-arylamide from amide through a C–N coupling process, albeit under harsh conditions limiting its broad application in organic synthesis.
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