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Rapid Oxygen Atom Transfer at a Catalysis-Relevant Ni(I)–Alkyl Complex with N<sub>2</sub>O

Ana Mateos-Calbet, Paolo Cleto Bruzzese, Markella Aliki Mermigki, Alexander Schnegg, Dimitrios A. Pantazis, Josep Cornellà

2025Journal of the American Chemical Society7 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide To improve our understanding of Ni-catalyzed alcohol formation with N 2 O, a catalytically relevant Ni(I)–alkyl was synthesized and characterized (EPR, NMR). The complex, prepared via comproportionation and transmetalation, reacted with N 2 O at ambient temperature within 1 min, producing alcohol and N 2 . This contrasts sharply with slower reactions of (bpy)NiEt 2 (12 h) and catalytic systems (22 h). Theoretical studies suggest a stepwise organometallic Baeyer–Villiger mechanism via a Ni(II)–oxyl intermediate. The high reactivity of Ni(I)–alkyl challenges the notion of N 2 O’s inertness, highlighting its potential as a versatile oxidant in synthesis.

Topics & Concepts

ChemistryAlkylOxygen atomCatalysisOxygenAtom (system on chip)StereochemistryOrganic chemistryMoleculeComputer scienceEmbedded systemMetal-Catalyzed Oxygenation MechanismsCO2 Reduction Techniques and CatalystsElectrocatalysts for Energy Conversion
Rapid Oxygen Atom Transfer at a Catalysis-Relevant Ni(I)–Alkyl Complex with N<sub>2</sub>O | Litcius