Palladium-Catalyzed Synthesis of (Hetero)Aryl Alkyl Sulfones from (Hetero)Aryl Boronic Acids, Unactivated Alkyl Halides, and Potassium Metabisulfite

A palladium‐catalyzed one‐step synthesis of (hetero)aryl alkyl sulfones from (hetero)arylboronic acids, potassium metabisulfite, and unactivated or activated alkylhalides is described. This transformation is of broad scope, occurs under mild conditions, and employs readily available reactants. A sto...

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Bibliographic Details
Published in:Angewandte Chemie 2015-11, Vol.127 (46), p.13775-13779
Main Authors: Shavnya, Andre, Hesp, Kevin D., Mascitti, Vincent, Smith, Aaron C.
Format: Article
Language:eng ; ger
Subjects:
Acids
Alkylierungen
Boronsäuren
Catalysis
Chemistry
Diffraction
Halides
Homogene Katalyse
Palladium
Potassium
Sulfone
Sulfones
Synthesis
Transformations
X-rays
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Summary:A palladium‐catalyzed one‐step synthesis of (hetero)aryl alkyl sulfones from (hetero)arylboronic acids, potassium metabisulfite, and unactivated or activated alkylhalides is described. This transformation is of broad scope, occurs under mild conditions, and employs readily available reactants. A stoichiometric experiment has led to the isolation of a catalytically active dimeric palladium sulfinate complex, which was characterized by X‐ray diffraction analysis. Alkylsulfonylierung in einem Schritt: Die hier vorgestellte Pd‐katalysierte Synthese von (Hetero)arylalkylsulfonen aus (Hetero)arylboronsäuren, K2S2O5 und Alkylhalogeniden ist breit einsetzbar, verläuft unter milden Bedingungen und nutzt einfach zugängliche Reaktanten. Ein stöchiometrischer Ansatz ermöglichte die Isolierung und Charakterisierung eines katalytisch aktiven dimeren Pd‐Sulfinat‐Komplexes.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201505918