Catalytic Aerobic N-Nitrosation by Secondary Nitroalkanes in Water: A Tandem Diazotization of Aryl Amines and Azo Coupling
Karu Ramesh, Hun Young Kim, Kyungsoo Oh
Abstract
Secondary nitroalkanes underwent oxygen-mediated nitro-nitrite isomerization, serving as versatile N-nitrosating agents under aerobic conditions. To capitalize on the newly discovered aerobic nitro-nitrite isomerization phenomenon, a phase-transfer catalysis system employing KSeCN and TBAI was developed, in which the tandem diazotization and azo coupling with nitroalkanes as well as N-nitrosation of amines were accomplished. The current tandem diazotization and azo coupling strategy provides a facile synthesis of areneazo-2-(2-nitro)propane derivatives, a safe synthetic alternative to aryl diazonium salts.
Topics & Concepts
ChemistryNitrosationCatalysisTandemArylCoupling (piping)Combinatorial chemistryOrganic chemistryAlkylMechanical engineeringComposite materialMaterials scienceEngineeringAmmonia Synthesis and Nitrogen ReductionAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions