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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Visible light mediated organocatalytic dehydrogenative aza-coupling of 1,3-diones using aryldiazonium salts
Ramanand Das1, Taraknath Kundu1, Joneswar Basumatary2
1Department of Chemistry, National Institute of Technology Sikkim Ravangla, South Sikkim PIN 737139 India taraknath.kundu@nitsikkim.ac.in.
Abstract:
An efficient protocol for diazenylation of 1,3-diones under photoredox conditions is presented herein. C-N bond forming Csp -H functionalization of cyclic and alkyl diones by unstable aryl diazenyl radicals is achieved through reaction with aryldiazonium tetrafluoroborates by organocatalysts under visible light irradiation. The reaction has wide substrate scope, gives excellent yields, and is also efficient in water as a green solvent. This method provides an easy access to aryldiazenyl derivatives that are useful key starting materials for the synthesis of aza heterocycles as well as potential pharmacophores.
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