Abstract
The major goal of the Chapter is to review developments in the use of Ru-porphyrin complexes as homogeneous (or matrix-supported) catalysts for oxygenation and oxidation processes. The subject was given impetus with the discovery of a remarkable reaction in which a Ru(II) porphyrin complex reacted with O2 to give a trans-dioxo-Ru(VI) species. Such species, which can be formed from a wide range of O-atom donors, were shown subsequently to be capable of acting as a bis(monooxygenase) in transferring both the coordinated oxo ligands (as O-atoms) to olefinic substrates, saturated hydrocarbons, phosphines, and thioethers, and the processes become catalytic in the presence of excess of the O-atom donor. Further, the dioxo species can also exhibit oxidase-like activity, and effect stoichiometric or catalytic oxidative-dehydrogenation of phenols, alkoxyarenes, alcohols, and amines. Use of chiral porphyrins has led to catalytic, asymmetric epoxidation and hydroxylations, even though radical intermediates are invoked, as well as oxygenation of racemic substrates (phosphines and more interestingly tertiary alkanes) to yield chiral products by kinetic resolution processes. The reaction mechanisms invoked range from genuine O-atom transfer (from RuVI, RuV, or RuIV species, where the disproportionation reaction [2 O=RuIV⇋RuII+O=RuVI=O] is important), to free-radical induced processes, particularly when the porphyrin ligands are extensively halogenated, as Ru complexes generally of such porphyrins are extremely active in radical-type decomposition of hydroperoxides, often present as trace impurities in hydrocarbon substrates.
The amine dehydrogenation chemistry has led to characterization of Ru-imine, -imido (i.e. nitrene), -oxo(imido), -amido, as well as -amine complexes, the types of species that are intermediates in some reductive enzyme processes, and in reactions such as oxyamination, amination, and aziridination; the last mentioned process involves transfer of the imido moiety (isoelectronic with the oxo group), and corresponding catalytic aziridination of alkenes and insertion of the imido group into alkanes to give amides can be catalyzed by Ru-porphyrin complexes; with chiral porphyrins, chiral recognition in binding of racemic aminoesters has been realized and enantioeselective amidation of hydrocarbon substrates has been demonstrated.
The beginning of the Chapter gives a general introduction to catalyzed oxygenation/oxidation reactions involving O2, and briefly describes enzymatic oxygenase and oxidase systems, particularly the monooxygenase, cytochrome P-450, as the attempted modelling of this system using Ru-porphyrin complexes led to the discovery of the trans-dioxo-Ru(VI) species and their chemistry.
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Ezhova, M.B., James, B.R. (2003). Catalytic oxidations using ruthenium porphyrins. In: Simándi, L.I. (eds) Advances in Catalytic Activation of Dioxygen by Metal Complexes. Catalysis by Metal Complexes, vol 26. Springer, Boston, MA. https://doi.org/10.1007/0-306-47816-1_1
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