Journal ArticleDOI
State of the art in the development of biomimetic oxidation catalysts
TLDR
The first biomimetic oxidations were achieved using the special oxygen donor iodosylbenzene, but cheaper and generally available oxidants such as sodium hypochlorite or hydrogen peroxide are presently used as the oxidants.Abstract:
Work during the last decade laid down the basis for biomimetic oxidation catalysis, which has become an established technique. Preliminary work relied on the use of metal complexes of 5,10,15,20-tetrakisphenylporphyrin (TPP), but these proved to be inadequate to perform the catalytic function. Further, derivatives of TPP with suitable and adequately positioned substituents, allowed the preparation of high performance catalysts, in terms of catalytic efficiency and stability, for some selected oxidations under specific reaction conditions and for a diversity of oxygen donors. The first oxidations were achieved using the ‘special’ oxygen donor iodosylbenzene, but cheaper and generally available oxidants such as sodium hypochlorite or hydrogen peroxide are presently used as the oxidants. Catalysts capable of promoting stereoselective catalysis are reported. Conditions for the efficient use of the catalysts so far reported require particular specificities and the catalytic activity is only shown, in the majority of the reported works, in the presence of selected species to act as axial ligands to the metal ion of the catalyst. Specific porphyrin structures were reported where the addition of a specific axial ligand can be avoided.read more
Citations
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Journal ArticleDOI
Artificial Enzymes Formed through Directed Assembly of Molecular Square Encapsulated Epoxidation Catalysts
TL;DR: The "molecular square" takes on the functions of the protein superstructure in an enzyme: it spatially protects the catalytic core from decomposition and induces reaction selectivity.
Journal ArticleDOI
Metalloporphyrin-based oxidation systems: from biomimetic reactions to application in organic synthesis
Chi-Ming Che,Jie-Sheng Huang +1 more
TL;DR: A series of ruthenium porphyrin catalysts, including those immobilized onto insoluble supports and covalently attached to soluble supports, promote the oxidation of a wide variety of organic substrates in up to >99% yields, with high regio-, chemo- and/or stereoselectivity.
Journal ArticleDOI
Porphyrin-containing molecular squares: Design and applications
Suk Joong Lee,Joseph T. Hupp +1 more
TL;DR: Coordinative directed assembly has been used by a number of research groups to obtain molecular squares featuring porphyrin components as discussed by the authors, and the syntheses and functional behavior of these compounds are reviewed.
Journal ArticleDOI
Oxidation of alkanes and alkenes by iodosylbenzene and hydrogen peroxide catalysed by halogenated manganese porphyrins in homogeneous solution and covalently bound to silica
TL;DR: In this article, the perchlorinated manganese porphyrin ring stabilizes Mn(II) and unfavour the formation of the active species, Mn V O.
Journal ArticleDOI
Metalloporphyrins: Bioinspired Oxidation Catalysts
TL;DR: A review of the use of solely molecular oxygen as an environmentally benign oxidant source, in oxidation reactions catalyzed by bio-inspired metalloporphyrin analogues can be found in this article.
References
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PatentDOI
First practical method for asymmetric epoxidation
Tsutomu Katsuki,K. B. Sharpless +1 more
TL;DR: In this article, a metal alkoxide is used as a catalyst, where the metal has a coordination number of at least four, and at least one, usually two, of the alkoxide groups bonded to the metal are bonded to asymmetric carbon atoms.
Journal ArticleDOI
Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage
Journal ArticleDOI
Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization
TL;DR: The use of 3A or 4A molecular sieves substantially increases the scope of the titanium(IV)-catalyzed asymmetric epoxidation of primary allylic alcohols as mentioned in this paper.
Journal ArticleDOI
The Osmium-Catalyzed Asymmetric Dihydroxylation: A New Ligand Class and a Process Improvement
K. Barry Sharpless,Willi Amberg,Youssef L. Bennani,Gerard A. Crispino,Jens Hartung,Kyu Sung Jeong,Hoi-Lun Kwong,Kouhei Morikawa,Zhi-Min Wang +8 more
TL;DR: In this paper, two key improvements in the osmiuun-catalyzed asymmetric dihydroxylation have led to a simple procedure which is applicable to a wide range of olefins.
Journal ArticleDOI
Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions
TL;DR: In this article, a new synthetic strategy for preparing tetraphenylporphyrins is presented, which should greatly expand synthetic entries into porphyrin-containing model systems, and is complementary to the Adler-Longo procedure.