Mechanistic comparison between Pd-catalyzed ligand-directed C-H chlorination and C-H acetoxylation.
This communication describes detailed investigations of the mechanism of the Pd-catalyzed C-H chlorination and acetoxylation of 2-o-tolylpyridine. Under the conditions examined, both reactions proceed via rate-limiting cyclopalladation. However, substrate and catalyst order as well as Hammett data indicate that the intimate mechanism of cyclopalladation differs significantly between PdCl2-catalyzed chlorination and Pd(OAc)2-catalyzed acetoxylation.
Stowers
Kara J
KJ
University of Michigan, Department of Chemistry, 930 North University, Ann Arbor, Michigan 48109-1055, USA.
Sanford
Melanie S
MS
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D006859:Hydrogen / Q000737:chemistry*; D008024:Ligands; D010165:Palladium / Q000737:chemistry*; D013388:Succinimides / Q000737:chemistry
D008024:Ligands; D013388:Succinimides; D010165:Palladium; D002244:Carbon; D006859:Hydrogen