Journal
ACS CATALYSIS
Volume 9, Issue 12, Pages 10940-10950Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b02326
Keywords
copper amine oxidase; bioinspired catalysis; topoquinone; amine oxidation; mechanism
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Funding
- SERB, New Delhi through a J. C. Bose Fellowship [SB/S2/JCB-85/2014]
- Science and Engineering Research Board New Delhi [CRG/2018/000430]
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Copper amine oxidase (CAO), consisting of the topoquinone (TPQ) cofactor, catalyzes the oxidation of primary amines to aldehyde. We have successfully addressed this issue through isolation of a copper complex which mimics the active-site structure as well as the function of CAO. This inimitable complex, consisting of two TPQ-like side-arms, formed by ambient aerial oxidation of a precursor Schiff base complex, is the most efficient homogeneous catalyst for quantitative oxidation of primary benzylic amines to corresponding secondary imines under ambient conditions within 30 min. The longstanding contention of actual involvement of Cu(II) in the catalysis is resolved through quenching experiments of Cu(II) superoxo species and detailed density functional theory studies.
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