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J Am Chem Soc. 2008 Oct 8;130(40):13285-93. doi: 10.1021/ja8045519. Epub 2008 Sep 10.

Insights into directing group ability in palladium-catalyzed C-H bond functionalization.

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Chemistry Department, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, USA.


This paper describes a detailed investigation of factors controlling the dominance of a directing group in Pd-catalyzed ligand-directed arene acetoxylation. Mechanistic studies, involving reaction kinetics, Hammett analysis, kinetic isotope effect experiments, and the kinetic order in oxidant, have been conducted for a series of different substrates. Initial rates studies of substrates bearing different directing groups showed that these transformations are accelerated by the use of electron-withdrawing directing groups. However, in contrast, under conditions where two directing groups are in competition with one another in the same reaction flask, substrates with electron-donating directing groups react preferentially. These results are discussed in the context of the proposed mechanism for Pd-catalyzed arene acetoxylation.

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