The catalytic cross-coupling of unactivated arenes.
The industrially important coupling of aromatic compounds has generally required differential prefunctionalization of the arene coupling partners with a halide and an electropositive group. Here we report that palladium, in conjunction with a copper oxidant, can catalyze the cross-coupling of N-acetylindoles and benzenes in high yield and high regioselectivity across a range of indoles without recourse to activating groups. These reactions are completely selective for arene cross-coupling, with no products arising from indole or benzene homo-coupling detected by spectroscopic analysis. This efficient reactivity should be useful in the design of other oxidative arene cross-couplings as well.
Stuart
David R
DR
Center for Catalysis Research and Innovation, University of Ottawa, Department of Chemistry, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
Fagnou
Keith
K
D001554:Benzene / Q000737:chemistry; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D010165:Palladium / Q000737:chemistry
D006841:Hydrocarbons, Aromatic; D007211:Indoles; D010165:Palladium; C030374:indole; D001554:Benzene