title: Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.
abstract: Using a high-throughput experimentation approach we found a selective and mild Pd-catalyzed oxidative coupling reaction between anilide derivatives and acrylates that occurs through ortho C-H bond activation. The reaction is carried out in an acidic environment and occurs even at room temperature with use of a cheap oxidant (benzoquinone) in yields up to 91%. The benzoquinone possibly also functions as a ligand, stabilizing the catalyst. From the electronic dependence of the reaction and the observed kinetic isotope effect (kH/kD = 3) the key step of the catalytic cycle is believed to be electrophilic attack by a [PdOAc]+ complex on the pi-system of the arene.
authors.affiliation: Institute of Molecular Chemistry, Faculty of Science, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands.
authors.forename: Maarten D K
authors.initials: MD
authors.lastname: Boele
authors.forename: Gino P F
authors.initials: GP
authors.lastname: van Strijdonck
authors.forename: André H M
authors.initials: AH
authors.lastname: de Vries
authors.forename: Paul C J
authors.initials: PC
authors.lastname: Kamer
authors.forename: Johannes G
authors.initials: JG
authors.lastname: de Vries
authors.forename: Piet W N M
authors.initials: PW
authors.lastname: van Leeuwen