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Synthesis, characterization and Pd(II)-coordination chemistry of the ligand tris(quinolin-8-yl)phosphite. Application in the catalytic aerobic oxidation of amines

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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. This complex is an efficient catalyst for the solvent-free mild oxidative coupling of primary amines to imines using air as an oxidant, obtaining moderate to good yields (up to 99%) and turnover numbers (TONs up to 230). This catalyst can be recovered from the reaction mixture and reused in a subsequent run without a 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 insight into the reactivity of the Pd(II)–P(Oquin)3 complex toward benzylamine.

Graphical abstract: Synthesis, characterization and Pd(ii)-coordination chemistry of the ligand tris(quinolin-8-yl)phosphite. Application in the catalytic aerobic oxidation of amines

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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., 2018, Advance Article
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    Synthesis, characterization and Pd(II)-coordination chemistry of the ligand tris(quinolin-8-yl)phosphite. Application in the catalytic aerobic oxidation of amines

    R. E. Rodríguez-Lugo, M. A. Chacón-Terán, S. De León, M. Vogt, A. J. Rosenthal and V. R. Landaeta, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C7DT04000H

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