Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction

doi:10.6023/cjoc202211039

Abstract

Cp*Rh(III) catalysts have shown excellent performance in the field of inert C—H bond functionalization because of their high activity and stability under mild conditions. However, limited by the number of Rh(III) coordination orbitals, the ligand studies in Cp*Rh(III) catalytic system are relatively few. Recently, our research group has been focusing on the external ligands promoted C—H bond functionalization with high activity and selectivity. In this review, the related works of Cp*Rh(III) catalyzed C—H bond functionalization are systematically summarized, including both symmetric and asymmetric C—H activation, the role of ligands in the Cp*Rh(III) catalytic system is discussed, and some reaction mechanisms are briefly described.

Key words: Cp*Rh(III), C—H bond functionalization, ligands

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Yannian Pan, Xiao Qin, Chengkai Yuan, Yi Lu. Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 924-948.

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Fig. & Tab. 34

Scheme 1. Cp*Rh(III)-catalyzed C—H bond functionalization

Scheme 2. Rh(III)-catalyzed alkenylation reaction of benzamide ortho-position C(sp2)—H bond

Scheme 3. Rh(III)-catalyzed Heck reaction of aldehyde C(sp2)—H bond

Scheme 4. Cp*Rh(III)-catalyzed oxidative coupling reaction of C(sp2)—H bond with alkenes

Scheme 5. Rh(III)-catalyzed three-step consecutive C—H functionalization under mild condition

Scheme 6. Gram scale synthesis and proposed reaction mechanism

Scheme 7. [Cp*RhCl2]2-catalyzed oxidative coupling reaction of phenylpyrazoles and internal alkynes

Scheme 8. Alkynylation of N-pentafluorophenyl benzoamides under mild condition

Scheme 9. Rh(III)-catalyzed [3+2] cyclization of ketoimides and diphenylacetylenes

Scheme 10. Rh(III)-catalyzed C—H arylation reaction of arenes and ArBpin

Scheme 11. Rh(III)-catalyzed β- or γ-C(sp3)—H arylation reaction directed by trimethylpyrazole

Scheme 12. Rh(III)-catalyzed selective mono- and diarylation of 8-methylquinolines with organoborons

Scheme 13. Rh(III)-catalyzed C—C bond formation of quinoline N?oxides at the C(8) position

Scheme 14. Cp*Rh(III)-catalyzed alkylation of 2-anilinopyrimidines and 2-phenoxypyrimidines with α-diazo esters

Scheme 15. Cp*Rh(III)-catalyzed C(6)-selective arylation of 2?pyridones with quinone diazides

Scheme 16. Rh(III)-catalyzed arylation of 8-methy/formylquinolines with diazo compounds

Scheme 17. Rh(III)-catalyzed hydrazine-directed C(sp2)—H amination

Scheme 18. Rh(III)-catalyzed amination of weakly-directing amide substrates with free secondary amines and anilines

Scheme 19. Rh(III)-catalyzed sp2 thiolation promoted by MPAAs

Scheme 20. Thiolation reaction mechanism

Scheme 21. Rh(III)-catalyzed thioacetal-directed C(sp3)—H amidation

Scheme 22. Rh(III)-catalyzed carbonyl-directed C(sp3)—H bond amidation

Scheme 23. Rh(III)-catalyzed C(sp2)—H addition to C=N and C=O

Scheme 24. Rh(III)-catalyzed C(sp3)—H bond acylation of 8-methylquinolines

Scheme 25. RhCl3?3H2O-catalyzed C(sp2)—H bond direct carboxylation

Scheme 26. C—H bond enantioselective functionalization controlled by chiral Cp

Scheme 27. CCA-enabled asymmetric alkylation of diarylmethylamines with dimethyl diazomalonates

Scheme 28. CCA-enabled enantioselective amideation of benzyl methylene of 8-alkyl quinolones

Scheme 29. CCA-enabled C(sp3)—H activation to form enantioselective C—C bond

Scheme 30. CCA-enabled asymmetric amidation of 2-alkyl pyridines with dioxazoldones

Scheme 31. Chiral CpRh(III) coordinates with CCA to catalyze the asymmetric [3+2] annulation of N-sulfonyl ketimines and alkynes

Scheme 32. Chiral CpRh(III) coordinates with CCA to catalyze the reaction of diaryl sulfoximines with diazo compounds

Scheme 33. Chiral CpRh(III) coordinates with CCA to catalyze cross-coupling reaction of 1?aryl isoquinoline derivatives with electron-rich heteroarenes

Scheme 34. Chiral CpRh(III) coordinates with CCA to catalyze the direct annulation reactions between 1-aryl isoquinoline derivatives and alkynes

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配体在Cp*Rh(III)催化C—H键官能团化反应中的应用