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Bioinspired Olefin cis-Dihydroxylation and Aliphatic C-H Bond Hydroxylation with Dioxygen Catalyzed by a Nonheme Iron Complex. | LitMetric

Bioinspired Olefin cis-Dihydroxylation and Aliphatic C-H Bond Hydroxylation with Dioxygen Catalyzed by a Nonheme Iron Complex.

Inorg Chem

Department of Inorganic Chemistry , Indian Association for the Cultivation of Science , 2A and 2B Raja S. C. Mullick Road , Jadavpur, Kolkata 700032 , India.

Published: August 2018

AI Article Synopsis

  • A mononuclear iron(II) complex, [(Tp)Fe(benzilate)], has been isolated for research on its ability to catalyze reactions, particularly the oxidation of organic compounds with oxygen.
  • The reaction converts benzilate into benzophenone while reducing dioxygen, with differing products formed based on other chemicals added to the reaction, such as protic or Lewis acids.
  • This iron(II) complex has been shown to effectively hydroxylate olefins and oxygenate C-H bonds in aliphatic compounds, with enhanced catalytic performance when a Lewis acid is present.

Article Abstract

A mononuclear iron(II)-α-hydroxy acid complex [(Tp)Fe(benzilate)] (Tp = hydrotris(3-phenyl-5-methylpyrazol-1-yl)borate) of a facial tridentate ligand has been isolated and characterized to explore its catalytic efficiency for aerial oxidation of organic substrates. In the reaction between the iron(II)-benzilate complex and O, the metal-coordinated benzilate is stoichiometrically converted to benzophenone with concomitant reduction of dioxygen on the iron center. Based on the results from interception experiments and labeling studies, different iron-oxygen oxidants are proposed to generate in situ in the reaction pathway depending upon the absence or presence of an external additive (such as protic acid or Lewis acid). The five-coordinate iron(II) complex catalytically cis-dihydroxylates olefins and oxygenates the C-H bonds of aliphatic substrates using O as the terminal oxidant. The iron(II) complex exhibits better catalytic activity in the presence of a Lewis acid.

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Source
http://dx.doi.org/10.1021/acs.inorgchem.8b01353DOI Listing

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