1052101-91-3Relevant articles and documents
Insights into directing group ability in palladium-catalyzed C-H bond functionalization
Desai, Lopa V.,Stowers, Kara J.,Sanford, Melanie S.
supporting information; experimental part, p. 13285 - 13293 (2009/02/06)
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.
