Cannizzaro reaction via electrolysis

Question

As cannizzaro reaction reaction is a redox reaction carried by adding base to an aldehyde, is it possible to carry out the reaction using electrolysis where graphite anode and copper cathode is used. Is it possible to carry out electrolysis of benzaldehyde in water solution to get benzoic acid and benzyl alcohol?

Answer 1

Let's start with reduction processes. In his book, Alfred J. Fry states in § 6.1.3. (page 217) that :

The electrochemical reduction of carbonyl compounds to alcohols is of limited synthetic interest, in view of the wide variety of chemical reagents that can also effect this conversion.

But the electrochemical route is one of the best methods for preparation of pinacols derived from aryl aldehydes and diaryl ketones. They may be reduced to pinacols in alkaline or aprotid solvents : yields are usually high ($\pu{85\%}$)

The reduction of carbonyl compounds to saturated hydrocarbons in strong acids at cathodes of lead compares favorably with procedures like Clemmensen and Wolff-Kishner reactions in both yield and simplicity.

Let's now discuss electrochemical oxidations. In page 273, the same author points out that :

At present, electrochemical oxidation of organic compounds is not nearly as valuable a technique as is electrochemical reduction. This is due to the fact that the mechanism of anodic processes had been studied far less than cathodic processes. There is an exception : the Kolbe reaction, where salts of carboxylic acids result in dimeric products plus $\ce{CO2}$

Ref.: Albert J. Fry, Synthetic Organic Electrochemistry, Harper & Row Publishers, New York 1972, 336 p. Library of Congress Number 72-82902