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Synthesis, Characterization and Pd (II)-Coordination Chemistry of the Ligand Tris(quinolin-8-yl)phosphite. Application in Catalytic Aerobic Oxidation of Amines

Abstract

The synthesis and characterization of the ligand tris(quinolin-8-yl)phosphite, (P(Oquin)3), are described and its coordination chemistry toward the metal precursor [Pd(COD)Cl2] (COD = 1,5-cyclooctadiene, C8H12) is reported. A new Pd (II) - P(Oquin)3 metal complex was isolated and fully characterized ([Pd{P(Oquin)3}Cl2]), and its X-ray diffraction analysis shows that the phosphite ligand coordinates as a bidentate P-N chelate. The complex is an efficient catalyst for the solvent-free mild oxidative coupling of primary amines to imines using air as oxidant, obtaining moderate to good yields (up to 99%) and turnover numbers (TONs up to 230). The catalyst can be recovered from the reaction mixture and reused in a subsequent run without significant loss of activity. Kinetic measurements of the oxidation of benzylamine suggest that the rate law is r = kapp[BnNH2][cat] ([BnNH2] = molar concentration of benzylamine, [cat] = molar concentration of [Pd{P(Oquin)3}Cl2], kapp = k[O2]c = 0.756 L mol-1 h-1 = apparent rate constant). In situ NMR tests were performed to gain some insights on the reactivity of the Pd (II) - P(Oquin)3 complex toward benzylamine.

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Publication details

The article was received on 25 Oct 2017, accepted on 25 Dec 2017 and first published on 26 Dec 2017


Article type: Paper
DOI: 10.1039/C7DT04000H
Citation: Dalton Trans., 2017, Accepted Manuscript
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    Synthesis, Characterization and Pd (II)-Coordination Chemistry of the Ligand Tris(quinolin-8-yl)phosphite. Application in Catalytic Aerobic Oxidation of Amines

    R. E. Rodriguez-Lugo, M. A. Chacon-Teran, S. De Leon, M. Vogt, A. J. Rosenthal and V. R. Landaeta, Dalton Trans., 2017, Accepted Manuscript , DOI: 10.1039/C7DT04000H

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