Journal of Electroanalytical Chemistry, Vol.385, No.2, 235-239, 1995
Palladium-Catalyzed Electrochemical Reduction of Vinyl and Aryl Triflates
The reduction of vinyl and aryl triflates 1, in the presence of stoichiometric amounts of benzoic acid and catalytic amounts of PdCl2(PPh(3))(2) results in the formation of the corresponding alkenes and arenes 2. Most probably, the reaction proceeds via a catalytic cycle initiated by the one-step two-electron reduction of the palladium complex followed by oxidative addition of unsaturated triflates to the low-ligated zerovalent palladium complex Pd-0(PPh(3)Cl-. The resultant sigma-vinyl and sigma-arylpalladium(II) intermediate undergoes a one-step two-electron reduction to afford 2 in moderate to good yield, regenerating the low-ligated zerovalent palladium complex.
Keywords:ORGANIC ELECTROPHILES;ORGANOTIN REAGENTS;OXIDATIVE ADDITION;COUPLING REACTIONS;TRIFLUOROMETHANESULFONATES;DEOXYGENATION;MECHANISM;ALKENES;PHENOLS