Electrochemical carboxylation of benzylic carbonates: alternative method for efficient synthesis of arylacetic acids

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…Moreover, supercritical CO 2 820 and microemulsions 821 could be utilized for such processes. Aside from halides, it has been reported that benzyl alcohols 822 and benzyl carbonates 823 could also serve as substrates in electrochemical carboxylation reactions.…”

Transition Metal‐Free CO2 Fixation into New Carbon–Carbon Bonds

“…[53] Gennaro and co-workers developed the EC of benzyl chlorides 134 for the synthesiso f2 -phenylpropanoic acid derivatives 135 in excellent yields, aclass of compounds that exhibits interesting anti-inflammatory properties (Scheme 30 a). [55] In 2015, Senboku and co-workersi nvestigated the EC of organic halides 136 in DMF,a llowing the synthesis of amidoester derivatives 137 in moderate to good yields (33-78 %; Scheme 30 b). [55] In 2015, Senboku and co-workersi nvestigated the EC of organic halides 136 in DMF,a llowing the synthesis of amidoester derivatives 137 in moderate to good yields (33-78 %; Scheme 30 b).…”

Efficient Synthesis of Mandel Acetates by Electrochemical Carboxylation of Benzal Diacetates

“…In the course of our efforts to apply electrochemical technique to organic synthesis, we recently focused on benzal diacetate 1 , which can readily be prepared from benzaldehyde and acetic anhydride. It would be expected that electrochemical carboxylation of benzal diacetate 1 would proceed as a similar manner in reported electrochemical carboxylation of benzyl acetate and carbonate with remaining one acetoxy group at the benzylic position to obtain α‐acetoxyphenylacetic acid, mandel acetate 2 . As a result, we successfully carried out electrochemical carboxylation of benzal diacetate 1 to give mandel acetates 2 having substituents on the phenyl ring in good to excellent yields.…”