Y. Shvo, Vered Goldman-Lev
May 1, 2002
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0
Influential Citations
19
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract Allyl diethyl phosphate (ADP) was found to function as a stoichiometric hydrogen acceptor in a catalytic oxidation reaction of alcohols with Pd(OAc) 2 . A variety of acyclic primary and secondary alcohols were oxidized in good yields and under mild conditions to the corresponding aldehydes and ketones, in the presence of Na 2 CO 3 or K 2 CO 3 . Simple aliphatic primary alcohols yielded esters, exclusively. Polar ligand solvents (DMF, DMSO) were found to accelerate the reaction. Slow, but high yield reactions were encountered in THF and acetonitrile as solvents. The reactivity of several other allyl systems serving as H-acceptors, and several Pd compounds serving as catalysts, in the above oxidation reaction, was evaluated. It has been experimentally demonstrated (H-NMR) that ADP is capable of generating a π-allyl-Pd complex using a Pd(0) complex. Consequently, a catalytic cycle was proposed for the above oxidation reaction.