Recent Advances on C—H Functionalization via Oxidative Electrophotocatalysis

doi:10.6023/cjoc202311032

Abstract

Direct and selective functionalization of relatively inert C—H bonds is a long-standing challenge in synthetic chemistry. While many strategies have been developed to date, new approach that does not require the use of transition-metals and oxidants is in high demand. Recently, electrophotocatalysis has emerged as a powerful means to effect direct C—H functionalization and other types of challenging transformations under mild reaction conditions. The recent advances on electrophotocatalytic C—H functionalization via anode oxidation are highlighted with a focus on mechanistic aspects. Challenges and opportunities of this emerging field are also discussed.

Key words: electrophotocatalysis, electrochemistry, C—H functionalization, oxidation

Cite this article

Aman Hasil, Rui Chang, Juntao Ye. Recent Advances on C—H Functionalization via Oxidative Electrophotocatalysis[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 728-747.

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Fig. & Tab. 26

Figure 1. (a) Bond dissociation energies of different C—H bonds,[11] (b) comparisons between photocatalysis, electrocatalysis and electrophotocatalysis (EPC) using oxidation of a substrate (Sub) as an example, and (c) an overview of research on oxidative electrophotocatalytic C—H functionalization since 2019

Scheme 1. Electrophotocatalytic C—H alkylation of heteroarenes with an organotrifluoroborates

Scheme 2. Direct decarboxylative C—H functionalization of heteroarenes and proposed mechanism

Scheme 3. Electrophotochemical undirected C—H trifluoromethylation of unactivated arenes and heteroarenes

Scheme 4. Electrophotochemical trifluoromethylation of arenes using trifluoroacetic acid

Scheme 5. Electrophotocatalytic C—H silylation of heteroarenes through dehydrogenation cross-coupling

Scheme 6. Chloride-promoted electrophotochemical C—H silylation of heteroarenes

Scheme 7. Electrophotocatalytic enantioselective heteroarylcyanation of styrenes

Scheme 8. Electrophotocatalytic methods for the dehydrogenative cross-coupling of arenes with azoles

Scheme 9. Electrophotochemical C—H azolation of arenes using acridinium salt as photooxidants

Scheme 10. C—H amination reaction of arenes with carbamates by using DDQ as a photocatalyst

Scheme 11. Electrophotocatalytic diamination of vicinal C—H bonds

Scheme 12. Electrophotocatalytic Ritter-type amination of benzylic C—H bonds

Scheme 13. Electrophotocatalytic oxygenation of multiple adjacent C—H bonds

Scheme 14. Electrophotocatalytic enantioselective cyanation of benzylic C(sp3)—H bonds

Scheme 15. Electrophotochemical benzylic C(sp3)—H arylation or oxygenative arylation.

Scheme 16. Electrophotochemical manganese-catalyzed oxidative azidation of C(sp3)—H bonds

Scheme 17. Combined electrochemical/photochemical iodide-mediated process for C—H amination

Scheme 18. Accelerated electrophotocatalytic C(sp3)—H heteroarylation enabled by an efficient continuous-flow reactor

Scheme 19. Electrophotocatalytic oxidation of unactivated alcohols via flavin/thiourea co-catalysis

Scheme 20. Regioselective electrophotocatalytic C—H functionalization of ethers

Scheme 21. Electrophotochemical oxidative C(sp3)—H borylation of unactivated hydrocarbons

Scheme 22. Electrophotochemical synthesis of alkylated benzimidazo-fused isoquinolinones

Scheme 23. Electrophotocatalytic cross-coupling of heteroarenes and C(sp3)—H donors

Scheme 24. Dehydrogenative coupling of benzothiazole with strong C(sp3)—H bonds

Scheme 25. Electrophotochemical asymmetric dehydrogenative [2?＋?2] cycloaddition between C—C single and double bonds

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