Palladium‐Catalyzed Cross‐Coupling of Styrenes with Aryl Methyl Ketones in Ionic Liquids: Direct Access to Cyclopropanes | Zendy

Cotugno Pietro | Zendy; Monopoli Antonio | Zendy; Ciminale Francesco | Zendy; Milella Antonella | Zendy; Nacci Angelo | Zendy

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Palladium‐Catalyzed Cross‐Coupling of Styrenes with Aryl Methyl Ketones in Ionic Liquids: Direct Access to Cyclopropanes

Author(s) -

Cotugno Pietro,

Monopoli Antonio,

Ciminale Francesco,

Milella Antonella,

Nacci Angelo

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201408245

Subject(s) - catalysis , aryl , cyclopropanation , chemistry , substrate (aquarium) , palladium , ketone , methyl ketone , ionic liquid , medicinal chemistry , coupling (piping) , coupling reaction , photochemistry , organic chemistry , combinatorial chemistry , materials science , alkyl , oceanography , metallurgy , geology

The combined use of Pd(OAc) 2 , Cu(OAc) 2 , and dioxygen in molten tetrabutylammonium acetate (TBAA) promotes an unusual cyclopropanation reaction between aryl methyl ketones and styrenes. The process is a dehydrogenative cyclizing coupling that involves a twofold CH activation at the α‐position of the ketone. The substrate scope highlights the flexibility of the catalyst; a reaction mechanism is also proposed.

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