Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.
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.
Boele
Maarten D K
MD
Institute of Molecular Chemistry, Faculty of Science, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands.
van Strijdonck
Gino P F
GP
de Vries
André H M
AH
Kamer
Paul C J
PC
de Vries
Johannes G
JG
van Leeuwen
Piet W N M
PW