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Aerobic Oxidative Synthesis of Formamides from Amines and Bioderived Formyl Surrogates

Xingchao Dai, Yunyan Han, Haijun Jiao, Feng Shi, Jabor Rabeah, Angelika Brückner

2024Angewandte Chemie International Edition13 citationsDOIOpen Access PDF

Abstract

Abstract Herein we present a new strategy for the oxidative synthesis of formamides from various types of amines and bioderived formyl sources (DHA, GLA and GLCA) and molecular oxygen (O 2 ) as oxidant on g‐C 3 N 4 supported Cu catalysts. Combined characterization data from EPR, XAFS, XRD and XPS revealed the formation of single CuN 4 sites on supported Cu phen /C 3 N 4 catalysts. EPR spin trapping experiments disclosed ⋅OOH radicals as reactive oxygen species and ⋅NR 1 R 2 radicals being responsible for the initial C−C bond cleavage. Control experiments and DFT calculations showed that the successive C−C bond cleavage in DHA proceeds via a reaction mechanism co‐mediated by ⋅NR 1 R 2 and ⋅OOH radicals based on the well‐equilibrated Cu II and Cu I cycle. Our catalyst has much higher activity (TOF) than those based on noble metals.

Topics & Concepts

FormamidesChemistryRadicalElectron paramagnetic resonanceCatalysisBond cleavageOxygenOxidative phosphorylationCatalytic cycleReaction mechanismPhotochemistryMedicinal chemistryOrganic chemistryBiochemistryPhysicsNuclear magnetic resonanceOxidative Organic Chemistry ReactionsChemical Synthesis and ReactionsNanomaterials for catalytic reactions