Recent Advances in Electrochemical Carboxylation of Inert Chemical Bonds with Carbon Dioxide

doi:10.6023/cjoc202406045

Abstract

Carbon dioxide (CO₂) is a green and renewable C1 synthon, and the direct carboxylation of inert chemical bonds with CO₂ could afford high value-added carboxylic acid derivatives from simple molecules, which feature both atomic and step economies. Organic electrosynthesis is a green synthesis technology using electrons as "reagents", and the development of electrochemical carboxylation of inert bonds with CO₂ has become a hot research topic in recent years. The recent progress on the electroreductive carboxylation of inert bonds with CO₂ is summarized, including C—H, C—C, C—O, and C—F single bonds. The mechanism and application of these reactions are emphatically discussed, and the challenges and development trends in this field are also covered.

Key words: carbon dioxide, inert chemical bonds, electrochemistry, reductive carboxylation, carboxylic acids

Cite this article

Xiaotong Gao, Yuqing Zhong, Nan Feng, Ying Sun, Deyong Yang, Feng Zhou. Recent Advances in Electrochemical Carboxylation of Inert Chemical Bonds with Carbon Dioxide[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3043-3062.

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Fig. & Tab. 23

Figure 1. BDEs of representative C—H, C—C, C—O and C—F inert bonds

Figure 2. Electroreductive carboxylation of inert bonds with CO2

Scheme 1. Site-selective electrochemical carboxylation of C—H bonds in N-heteroarenes

Scheme 2. Site-selective electrochemical carboxylation of C—H bonds in arenes

Scheme 3. Electrocatalytic carboxylation of benzylic C—H bonds in aromatic alcohols

Scheme 4. Electrochemical ring-opening dicarboxylation of C—C single bonds in strained rings

Scheme 5. Electrochemical ring-opening carboxylation of C—C bonds in gem-difluorocyclopropanes

Scheme 6. Electrochemical ring-opening carboxylation of C—C bonds in cycloketone oxime esters

Scheme 7. Electrochemical regioselective carboxylation of C—O single bonds in allyl esters

Scheme 8. Electrocarboxylation of C—O single bonds in allyl esters

Scheme 9. Electrocarboxylation of C—O single bonds in propargylic acetates

Scheme 10. Asymmetric electrocatalytic carboxylation of C—O single bonds in propargylic carbonates

Scheme 11. Electrocarboxylation of C—O single bonds in benzal diacetates

Scheme 12. Electrocarboxylation of C—O single bonds in benzylic phosphates and phosphinates

Scheme 13. Electrocarboxylation of C—O single bonds in aryl methanols

Scheme 14. Micro-electro-flow induced carboxylation of C—O single bonds in biphenylmethanol

Scheme 15. Electrocarboxylation of C—O single bonds in epoxides

Scheme 16. Electrochemical carboxylation of C—O single bonds in aryl epoxides

Scheme 17. Electrocarboxylation of C(sp3)—O single bonds in 1,3-oxazolidin-2-ones

Scheme 18. Electrocarboxylation of C—O single bonds in cyclic carbonate

Scheme 19. Electrochemical defluorinative carboxylation of C—F bonds in α-CF3 alkenes

Scheme 20. Electrochemical defluorinative carboxylation of C—F bonds in gem-difluoroalkenes

Scheme 21. Electrochemical defluorinative carboxylation of C—F bonds in trifluoromethyl (hetero)arenes

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