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Metal‐free Decarboxylative Annulation of 2‐Aryl‐2‐isocyano‐acetates with Aryldiazonium Salts: General Access to 1,3‐Diaryl‐1,2,4‐triazoles

Yu‐Ting Tian, Fa‐Guang Zhang, Jing Nie, Chi Wai Cheung, Jun‐An Ma

2020Advanced Synthesis & Catalysis21 citationsDOI

Abstract

Abstract Isocyanoacetates are versatile substrates for the synthesis of heterocyclic compounds, but the concomitant decarboxylation remains rare. Herein we report a decarboxylative annulation reaction of 2‐aryl‐2‐isocyanoacetates with aryldiazonium salts. This metal‐free, base‐promoted protocol allows for the access to a broad collection of 1,3‐diaryl‐1,2,4‐triazoles, including chiral triazole‐based binaphthalene ligands, drug mimics, and synthetic intermediates of druglike molecules. magnified image

Topics & Concepts

ChemistryAnnulationArylDecarboxylationCombinatorial chemistryMoleculeOrganic chemistryCatalysisAlkylCatalytic C–H Functionalization MethodsClick Chemistry and ApplicationsMulticomponent Synthesis of Heterocycles
Metal‐free Decarboxylative Annulation of 2‐Aryl‐2‐isocyano‐acetates with Aryldiazonium Salts: General Access to 1,3‐Diaryl‐1,2,4‐triazoles | Litcius