Analysis of the concerted metalation-deprotonation mechanism in palladium-catalyzed direct arylation across a broad range of aromatic substrates.
The concerted metalation-deprotonation mechanism predicts relative reactivity and regioselectivity for a diverse set of arenes spanning the entire spectrum of known palladium-catalyzed direct arylation coupling partners. An analysis following an active strain model provides a more complete portrayal of the important arene/catalyst parameters leading to a successful coupling. The breadth of arenes whose reactivity can be predicted by the CMD mechanism indicates that it may be far more widespread than previously imagined.
Gorelsky
Serge I
SI
Center for Catalysis Research and Innovation, University of Ottawa, Department of Chemistry, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5. sgorelsk@uottawa.ca
Lapointe
David
D
Fagnou
Keith
K
D002384:Catalysis; D008956:Models, Chemical; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011522:Protons; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013816:Thermodynamics; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry
D011522:Protons; D013438:Sulfhydryl Compounds; D013876:Thiophenes; D010165:Palladium