Recent Advances in the Oxidative Coupling Reaction of Enol Derivatives

doi:10.6023/cjoc202104058

Abstract

Oxidative coupling reaction of enol derivatives (enolates, enol silanes, enamines, etc.) provides an efficient method for the direct construction of carbon-carbon bond, which plays a prominent role in the field of synthetic chemistry. Although the first case of this reaction had been reported in 1935, it was not until the 1970s that chemists began to pay more attention to this reaction. However, the effectiveness and practicability of this reaction were still somewhat limited at that time. In recent years, this reaction has been developed rapidly in the field of synthetic methodology and the total synthesis of natural products. Therefore, these advances in methodologies and its applications in the total synthesis of natural products in the last decades are mainly summarized.

Key words: oxidative coupling reaction, enol derivatives, carbon-carbon bond, methodology, natural product

Cite this article

Wei Chen, Qiang Liu. Recent Advances in the Oxidative Coupling Reaction of Enol Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3414-3430.

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Fig. & Tab. 41

Scheme 1. Three types of the coupling reaction

Scheme 2. Oxidative coupling reaction of enol derivatives

Scheme 3. Oxidative cross-coupling reaction of enolates

Ketone A	Ketone B	Product C	A₂B₂/A₄+B₄	Product ratio	Yield/%

Table 1. Flowers' studies on Li-enolate aggregation effects of oxidative cross-coupling reaction

Scheme 4. Enantioselective oxidative homo-coupling reaction of titanium enolates

Scheme 5. Enantioselective synthesis of biphenol via oxidative homo-coupling reaction reported by Thomson's group

Scheme 6. First enantioselective oxidative cross-coupling reaction of enolates reported by Alezra's group

Scheme 7. Copper-catalyzed oxidative homo-coupling reaction of enolates reported by Daugulis's group

Scheme 8. Copper or silver-catalyzed syntheses of tetrasubstituted furans, thiophenes and pyrroles reported by Wang's group Reaction conditions: AgF (10 mol%), air, xylene, 140 ℃, 4~10 h; SET (single electron transfer)

Scheme 9. Cerium catalyzed oxidative cross-coupling reaction of enolates reported by Christoffers's group

Scheme 10. Iron-catalyzed catalyzed oxidative cross-coupling reaction of enolates reported by Ohshima and Takashi's group

Scheme 11. Catalytic asymmetric electrosynthesis of enantioenriched molecules from enolates reported by Meggers's group

Scheme 12. Intermolecular oxidative cross-coupling reaction of enol silanes reported by Ruzziconi's group

Scheme 13. First oxidative homo-coupling reaction of bis-enol silanes reported by Schmittel's group

Scheme 14. Intramolecular oxidative coupling reaction of bis- enol silanes reported by Thomson's group

Scheme 15. Stereoselective oxidative cross-coupling reaction of bis-enol silanes reported by Yang and Gong's group

Scheme 16. Electrochemical, manganese-assisted C—C bond formation reported by Hilt's group

Scheme 17. Proposed reaction mechanism for the Mn(TPA) dichloride mediated reaction reported by Hilt's group

Scheme 18. Intermolecular oxidative cross-coupling reaction of enamine and enol silane reported by Narasaka's group

Scheme 19. Enantioselective organocatalytic oxidative cross- coupling reaction reported by MacMillan's group

Scheme 20. Visible-light-promoted oxidative cross-coupling reaction of enamines reported by Akita and Koike's group

Scheme 21. Pyrroles synthesis via oxidative homo-coupling reaction of enamines reported by Jia's group

Scheme 22. Catalytic asymmetric oxidative γ-coupling of α,β- unsaturated aldehydes reported by Jørgensen's group

Scheme 23. Oxidative homo-coupling of boron enolate reported by Hirao's group

Scheme 24. Oxidative cross-coupling of boron enolate reported by Hirao's group

Scheme 25. Oxovanadium(V)-catalyzed oxidative cross-cou- pling of boron enolates reported by Hirao's group

Scheme 26. Total synthesis of (±)-wikstromol reported by Belletire's group

Scheme 27. Total synthesis of (–)-bursehernin reported by Baran's group

Scheme 28. Enantiospecific total synthesis of hapalindoles, fischerindoles, welwitindoles reported by Baran's group

Scheme 29. Synthesis of the core carbon skeleton of maoecrystal V reported by Baran's group

Scheme 30. Total synthesis of bismurrayaquinone A reported by Thomson's group

Scheme 31. Structures of lomaiviticin A and lomaiviticin B

Scheme 32. Synthesis of the core ring system of lomaiviticins reported by Shair's group

Scheme 33. Enantioselective synthesis of lomaiviticins aglycon reported by Herzon's group

Scheme 34. Total synthesis of (±)-folicanthine reported by Bisai's group

Scheme 35. Total synthesis of propindilactone G reported by Yang and Chen's group

Scheme 36. Total synthesis of (±)-hirsutene reported by Cohen and Ramig's group

Scheme 37. Total synthesis of stephacidin A, avrainvillamide and stephacidin B reported by Baran's group

Scheme 38. Total synthesis of (±)-actinophyllic acid reported by Overman's group

Scheme 39. Oxidative coupling strategies for the synthesis of indole alkaloids reported by Ma's group

Scheme 40. Total synthesis of (+)-7,20-diisocyanoadociane reported by Thomson's group

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