Cerium and ruthenium complexes containing oxygen donor ligands

  • Wai Ho WONG

Student thesis: Master's thesis

Abstract

Metal complexes with oxygen donor ligands are of interest because of their relevance to the active sites of oxide-based heterogeneous catalysts. In this thesis, metal complexes with chelating oxygen-donor ligands, including the Kläui tripodal ligand [(η5-C5H5)Co{P(O)(OEt)2}3]- (LOEt-) and perfluoropincolate [(CF3)4C2O2]2- (pinF), have been synthesized, and their redox and catalytic chemistry has been studied. Also, nitrido-bridged heterometallic iron(IV)/ruthenium(IV) porphyrin complexes have been synthesized and their use as catalysts for alkene epoxidation has been examined. In Chapter 2, Ce(IV) complexes with oxidizing oxyanion ligands have been synthesized and structurally characterized. Reaction of [(LOEt)2CeCl2] with NaIO4 in water afforded a Ce(IV) periodate complex, 2-2, the crystal of which was found to contain two independent molecules: [(LOEt)2Ce(IO4)2] (2-2a) and [(LOEt)2Ce(H2O)(IO4)][IO4] (2-2b). Treatment of [(LOEt)2CeCl2] with I2O5 in CH3CN in the presence of a trace amount of water led to isolation of the Ce(IV) iodate complex [(LOEt)2Ce(IO3)2]⋅H+ICl2- (2-3). Reaction of [(LOEt)2CeCl2] with K2S2O8 in water afforded the Ce(IV) persulfate complex [(LOEt)2Ce(S2O8)] (2-4). The cyclic voltammograms of complexes 2-2 – 2-4 in acetonitrile displayed quasi-reversible couples that are attributed to the Ce(III/IV) oxidation. The Ce(IV) periodate and iodate complexes can oxidize methyl p-tolyl sulfide to sulfoxide. A Ru-imidazolin-2-iminato complex has been synthesized by reaction of a Ru(VI) nitride with an N-heterocyclic carbene. Treatment of [LOEtRu(N)Cl2] with 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (ImDipp) afforded the Ru(IV) imidazolin-2-iminato complex [LOEtRu(NImDipp)Cl2] (3-2). Chloride abstraction of 3-2 with TIPF6 in CH2Cl2/MeCN gave [LOEtRu(NImDipp)(MeCN)Cl][PF6] (3-3). Oxidation of 3-2 with [(4-BrC6H4)3N][SbCl6] in CH2Cl2 afforded the Ru(V) complex [LOEtRuCl3](SbCl6)⋅(HNImDipp) (3-4). 3-2 and 3-3 exhibited the Ru(V/IV) couples at 0.05 and 0.71 V vs. Fc+/0 (Fc = ferrocene), respectively. Complexes 3-2 and 3-3 can catalyze the epoxidation of cyclooctene with PhIO, presumably via Ru-oxo intermediates. In Chapter 4, Ru-pinF complexes have been synthesized and structurally characterized. Treatment of (nBu4N)[Ru(N)Cl4] with Na2pinF resulted in the isolation of (nBu4N)[Ru(N)(pinF)Cl2] (4-1). Reaction of 4-1 with NaLOEt in MeOH afforded [(LOEt)Ru(N)(pinF)] (4-3). Reaction of 4-1 with K[N(Ph2PQ)2] (Q = S, Se) afforded [Ru(N)(pinF){N(Ph2PQ)2}] (Q = S (4-5), Se (4-6)). Reaction of 4-3 with PPh3 and ImDipp afforded [(LOEt)Ru(NX)(pinF)] (X = PPh3 (4-7), ImDipp (4-8)). Reaction of 4-3 with HBF4·Et2O led to isolation of [Ru(N)(pinF)]2(μ-OEt)2 (4-9). Complex 4-1 in conjunction with BF3 can catalyze the oxidation of cyclohexene, cyclooctene and ethylbezene with tert-butyl hydroperoxide, possibly via an F3B-N=Ru=O active species. Treatment of [Fe(TPP)Cl] (TPP2- = tetraphenylpoprhyrin dianion) with sodium naphthanide and [LOEtRu(N)Cl2] afforded [(TPP)Fe(μ-N)RuLOEtCl2] (5-1) that reacted with 4-tert-butylaniline (L) in CH2Cl2 to give [(L)(TPP)Fe(μ-N)RuLOEtCl2] (5-2). The crystal structures of 5-1 and 5-2 featuring linear Fe=N=Ru linkages have been determined. Complexes 5-1 and 5-2 can catalyze the oxidation of cyclooctene and cyclohexene with PhIO.
Date of Award2019
Original languageEnglish
Awarding Institution
  • The Hong Kong University of Science and Technology

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