Electrochemical Approaches to Carbonylative Coupling Reactions

Abstract

The carbonylation reaction is an effective way to introduce CO or other carbonyl groups into organic compounds, and widely used in the preparation of aldehydes, ketones, amides, and esters. The replacement of conventional reaction approaches by greener electrochemical methods is appealing with great synthetic potential as well as inherent safety, owing to the avoidance of external oxidants or reductants and a more facile control in product selectivity. In this minireview, we give a summary of the recent development of carbonylation reactions via the electrochemical approach.

Palladium-Catalyzed Carbonylations: Application in Complex Natural Product Total Synthesis and Recent Developments

“…Numerous examples have been reported that use oxygen (or air) as an oxidant or co-oxidant in conjunction with a copper salt, but for industrial applications this can raise the risk of an explosion. Electrochemical oxidation is an environmentally friendly solution which operates under mild conditions without the need for an external oxidant . Accordingly, electrochemical carbonylation methods are already starting to be developed.…”

“…Electrochemical oxidation is an environmentally friendly solution which operates under mild conditions without the need for an external oxidant. 35 Accordingly, electrochemical carbonylation methods are already starting to be developed. For example, in 2021 the Lei group developed an electrochemical palladium-catalyzed oxidative carbonylation of arylhydrazines and alkynes to ynones ( Figure 7 A).…”

Recent progress of Cu-based electrocatalysts for upgrading biomass-derived furanic compounds

“…2). 15,16 In these electrocatalytic processes, the reactive species of hydrogen (e.g., *H, * denotes an electrocatalytically active site) or oxygen (e.g., *OOH and *OH) in situ generated from water electrolysis can react with substrates towards alcohols/ alkanes via electrocatalytic hydrogenation (ECH) or carboxylic acids via electrocatalytic oxidation (ECO), respectively. 17,18 Moreover, they involve a series of radical processes that spawn electro-reductive/oxidative coupling for extending carbon chains.…”

Rhodium-catalyzed aminoacylation of alkenes via carbonylative C–H activation toward poly(hetero)cyclic alkylarylketones

“…Use of inexpensive CO as a versatile C1-synthon is widespread in academia and industrial processes. 1 Transition metal-catalyzed carbonylation reactions enable various carbonyl-containing compounds ( e.g. , acids, amides, esters, acyl halides, aldehydes, and ketones) can be constructed based on miscellaneous nucleophiles.…”