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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.

Mechanistic Comparison between Pd-Catalyzed Ligand-Directed C−H Chlorination and C−H Acetoxylation