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.
We describe a short and efficient synthetic route to euchrestifoline. Key steps of our approach are the iron(III)‐catalyzed Wacker‐type oxidation of a chromene derivative with hexadecafluorophthalocyanine‐iron (FePcF16) as catalyst, a palladium(0)‐catalyzed Buchwald–Hartwig amination, and the final palladium(II)‐catalyzed oxidative cyclization of the resulting diarylamine to the natural product.
Herein, we describe ac onvenient and general method for the oxidation of olefins to ketones using either tris(dibenzoylmethanato)iron(III) [Fe(dbm) 3 ]o racombination of iron(II) chloride and neocuproine (2,9-dimethyl-1,10phenanthroline) as catalysts and phenylsilane (PhSiH 3 )a s additive.All reactions proceed efficiently at room temperature using air as sole oxidant. This transformation has been applied to av ariety of substrates,i so perationally simple,p roceeds under mild reaction conditions,a nd shows ah igh functionalgroup tolerance.T he ketones are formed smoothly in up to 97 %y ield and with 100 %r egioselectivity,w hile the corresponding alcohols were observed as by-products.L abeling experiments showed that an incorporated hydrogen atom originates from the phenylsilane.T he oxygen atom of the ketone as well as of the alcohol derives from the ambient atmosphere.
The hexadecafluorophthalocyanine-iron complex FePcF 16 was recently shown to convert olefins into ketones in the presence of stoichiometric amounts of triethylsilane in ethanol at room temperature under an oxygen atmosphere. Herein, we describe an extensive mechanistic investigation for the conversion of 2-vinylnaphthalene into 2-acetylnaphthalene as model reaction. A variety of studies including deuterium-and 18 O 2 -labeling experiments, ESI-MS, and 57 Fe Mössbauer spectroscopy were performed to identify the intermediates involved in the catalytic cycle of the oxidation process. Finally, a detailed and well-supported reaction mechanism for the FePcF 16 -catalyzed Wacker-type oxidation is proposed.
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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