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Mild Amide <i>N</i>-Arylation Enabled by Nickel-Photoredox Catalysis

Robert D. Bradley, Ana Bahamonde

2022Organic Letters16 citationsDOIOpen Access PDF

Abstract

This paper describes a mild strategy to promote amide arylations. Photoinduced oxidation of a Ni(II) aryl amido intermediate is proposed to facilitate the challenging C-N reductive elimination step at moderate temperatures. Notably, the mildly basic conditions employed facilitate access to a broad scope including protected amino acids, heterocycles, phenols, and sterically hindered substituents. Hence, this work presents an attractive strategy to enable late-stage functionalization of pre-existing amide moieties in commercial drugs and natural products.

Topics & Concepts

ChemistryAmideArylCatalysisCombinatorial chemistrySteric effectsNickelPhenolsSurface modificationScope (computer science)Organic chemistryComputer scienceAlkylProgramming languagePhysical chemistryCatalytic Cross-Coupling ReactionsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Mild Amide <i>N</i>-Arylation Enabled by Nickel-Photoredox Catalysis | Litcius