Coupling Pd-Catalyzed Alcohol Oxidation to Olefin Functionalization: Hydrohalogenation/Hydroalkoxylation of Styrenes.
A hydrochlorination reaction of styrenes catalyzed by Pd(II) in combination with Cu(II) was developed, which was followed by an in situ conversion of electron-rich products to an ether in the presence of an alcohol. Mechanistic experiments indicate that olefin functionalization is coupled to an alcohol oxidation, wherein a Pd hydride formed in the β-hydride elimination step of the alcohol oxidation was incorporated into the product.
Department of Chemistry, University of Utah, 315 South, 1400 East, Salt Lake City, Utah 84112.
Susanne M
SM
Podhajsky
Matthew S
MS
Sigman