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 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.201408245
Subject(s) - aryl , catalysis , cyclopropanation , substrate (aquarium) , chemistry , ketone , ionic liquid , palladium , methyl ketone , flexibility (engineering) , medicinal chemistry , coupling (piping) , organic chemistry , materials science , oceanography , alkyl , geology , statistics , mathematics , metallurgy
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.