Iron Catalysis in Biological and Biomimetic Reactions

Müller, Jens; Bröring, Martin

doi:10.1002/9783527623273.ch2

Iron Catalysis in Organic Chemistry 2008

DOI: 10.1002/9783527623273.ch2

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Iron Catalysis in Biological and Biomimetic Reactions

Jens Müller

Martin Bröring

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Cited by 4 publications

References 260 publications

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Conversion of Olefins into Ketones by an Iron‐Catalyzed Wacker‐type Oxidation Using Oxygen as the Sole Oxidant

Puls

Knölker

2017

Angewandte Chemie

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We describe am ild and operationally simple procedure for the oxidation of olefins into ketones.T he reaction is catalyzedb yt he hexadecafluorinated iron-phthalocyanine complex FePcF 16 with stoichiometric amounts of triethylsilane as an additive under oxygen atmosphere to give ketones in good to high yields with excellent chemoselectivity and functional group tolerance.K etone formation proceeds in up to 95 %y ield and with 100 %r egioselectivity while the corresponding alcohols were observed as side products.

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Conversion of Olefins into Ketones by an Iron‐Catalyzed Wacker‐type Oxidation Using Oxygen as the Sole Oxidant

Puls

Knölker

2017

Angewandte Chemie

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Iron‐Catalyzed Wacker‐type Oxidation of Olefins at Room Temperature with 1,3‐Diketones or Neocuproine as Ligands**

et al. 2021

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Herein, we describe a convenient and general method for the oxidation of olefins to ketones using either tris(dibenzoylmethanato)iron(III) [Fe(dbm)3] or a combination of iron(II) chloride and neocuproine (2,9‐dimethyl‐1,10‐phenanthroline) as catalysts and phenylsilane (PhSiH3) as additive. All reactions proceed efficiently at room temperature using air as sole oxidant. This transformation has been applied to a variety of substrates, is operationally simple, proceeds under mild reaction conditions, and shows a high functional‐group tolerance. The ketones are formed smoothly in up to 97 % yield and with 100 % regioselectivity, while the corresponding alcohols were observed as by‐products. Labeling experiments showed that an incorporated hydrogen atom originates from the phenylsilane. The oxygen atom of the ketone as well as of the alcohol derives from the ambient atmosphere.

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Conversion of Olefins into Ketones by an Iron‐Catalyzed Wacker‐type Oxidation Using Oxygen as the Sole Oxidant

Puls

Knölker

2017

Angew Chem Int Ed

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We describe a mild and operationally simple procedure for the oxidation of olefins into ketones. The reaction is catalyzed by the hexadecafluorinated iron-phthalocyanine complex FePcF with stoichiometric amounts of triethylsilane as an additive under oxygen atmosphere to give ketones in good to high yields with excellent chemoselectivity and functional group tolerance. Ketone formation proceeds in up to 95 % yield and with 100 % regioselectivity while the corresponding alcohols were observed as side products.

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Iron Catalysis in Biological and Biomimetic Reactions

Cited by 4 publications

References 260 publications

Conversion of Olefins into Ketones by an Iron‐Catalyzed Wacker‐type Oxidation Using Oxygen as the Sole Oxidant

Conversion of Olefins into Ketones by an Iron‐Catalyzed Wacker‐type Oxidation Using Oxygen as the Sole Oxidant

Iron‐Catalyzed Wacker‐type Oxidation of Olefins at Room Temperature with 1,3‐Diketones or Neocuproine as Ligands**

Conversion of Olefins into Ketones by an Iron‐Catalyzed Wacker‐type Oxidation Using Oxygen as the Sole Oxidant

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