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Iron‐Catalyzed Wacker‐type Oxidation of Olefins at Room Temperature with 1,3‐Diketones or Neocuproine as Ligands **
Author(s) -
Puls Florian,
Linke Philipp,
Kataeva Olga,
Knölker HansJoachim
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202103222
Subject(s) - phenylsilane , chemistry , catalysis , regioselectivity , ketone , yield (engineering) , alcohol , alcohol oxidation , medicinal chemistry , photochemistry , organic chemistry , materials science , metallurgy
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 (PhSiH 3 ) 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.