Steric control of site selectivity in the Pd-catalyzed C-H acetoxylation of simple arenes
This report describes the use of an oxidant and a ligand to control site selectivity in the Pd(OAc)2-catalyzed C-H acetoxylation of simple arenes. The use of MesI(OAc)2 as the terminal oxidant in combination with acridine as the ligand results in primarily sterically controlled selectivity. In contrast, with Pd(OAc)2 as the catalyst and PhI(OAc)2 as the oxidant, electronic effects dominate the selectivity of arene C-H acetoxylation.
Cook, Amanda K.,Emmert, Marion H.,Sanford, Melanie S.
supporting information
p. 5428 - 5431
(2013/11/19)
Electrophilic components in the electrochemical acetoxylation of substituted arenes
The mechanism of anodic acetoxylation of substituted arenes under conditions of undivided galvanostatic electrolysis in MeCN containing acetate is suggested and an important role of electrophilic components (AcOH or ZnCl2) catalyzing transformation of intermediate ipso-acetoxylated polysubstituted arenonium cations to corresponding ortho-acetoxylated arenonium cations, which give acetoxylation products after deprotonation, is experimentally proved.
Burasov, Alexander V.,Petrosyan, Vladimir A.
p. 196 - 197
(2008/12/22)
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