Premium
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.