Recent Advances in the Reactions of β-Naphthol at α-Position

doi:10.6023/cjoc202207015

Abstract

β-Naphthol is an important synthon in organic synthesis and can participate in various chemical reactions due to its active chemical property at α-site, which has attracted a great attention from chemists. β-Naphthol can undergo various chemical transformations at α-position, such as alkylation, arylation, cyclization, amination, halogenation and so on, which can be used to construct structurally diverse naphthol derivatives with various biological activities. These naphthol derivatives can be used not only as the privileged skeletons of natural active drugs, but also as the building blocks for the preparation of the important intermediates in chemical synthesis. In recent years, chemical reactions based on β-naphthol at α-site have emerged one after another. The reactions of β-naphthol at α-position are reviewed from the aspects of C-C, C-N, C-O, C-X, C-S, C-P bond constructions and so on.

Key words: β-naphthol, α-position, C-C bond, C-X bond

Cite this article

Jing Liu, Jintao Chen, Tingting Liu, Jia Liu, Yaofu Zeng. Recent Advances in the Reactions of β-Naphthol at α-Position[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 379-410.

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Fig. & Tab. 60

Scheme 1. Friedel-Crafts reaction of β-naphthols with α-amino- sulfones

Scheme 2. Friedel-Crafts alkylation of β-naphthols with enamines

Scheme 3. Friedel-Crafts type dehydrative alkylation of β- naphthols with diarylmethanols

Scheme 4. Asymmetric Friedel-Crafts reaction of β-naphthols with aminocyclopropanes

Scheme 5. Aza-Friedel-Crafts reaction of β-naphthols with imines catalyzed by a binuclear zinc complex

Scheme 6. Asymmetric aza-Friedel-Crafts/N,O-acetalization of β-naphthols with pyrazolinone ketimines

Scheme 7. Aza-Friedel-Crafts reaction of β-naphthols with benzothiazolamides

Scheme 8. Synthesis of 1-carbamato-alkyl-2-naphthols via three-component reaction catalyzed by TCCA

Scheme 9. Iron trifluoroacetate catalyzed multicomponent reaction of naphthols, formaldehydes and anilines

Scheme 10. Michael addition reaction of β-naphthols with arenesulfonylalkylindoles

Scheme 11. Photocatalytic oxidative dehydrogenation coupling reaction of β-naphthols with glycine derivatives

Scheme 12. Dearomatic reaction of β-naphthols with 2-chlorocyclopentanone or 2-chlorocyclohexanone

Scheme 13. Dearomatic allylation reaction of β-naphthols

Scheme 14. Rhodium-catalyzed asymmetric allylic dearomatization of β-naphthols with aryl vinyl methanol

Scheme 15. Palladium-catalyzed allylic alkylation dearomatization of β-naphthol with gem-difluorinated cyclopropanes

Scheme 16. Palladium-catalyzed asymmetric domino Heck/dearomatization reaction of β-naphthols

Scheme 17. Gold-catalyzed intramolecular dearomatization reaction of β-naphthols via hydroalkylation process

Scheme 18. Copper-catalyzed stereoselective propargylic dearomatization of β-naphthols

Scheme 19. Arylation of β-naphthols with diaryliodonium salts

Scheme 20. Oxidative cross-coupling reaction of electron-rich phenols with β-naphthols

Scheme 21. Chiral phosphoric acid catalyzed asymmetric arylation of β-naphthols with quinone derivatives

Scheme 22. Br?nsted acid catalyzed direct arylation of β-naphthols with quinone monoacetal

Scheme 23. Quinine catalyzed coupling reaction of β-naphthols with halogenated quinones

Scheme 24. Tetrapeptide catalyzed coupling reaction of β-naphthols with quinone derivatives

Scheme 25. Br?nsted acid catalyzed heteroaryl reaction of β-naphthols with azines

Scheme 26. Photocatalytic arylation reaction of β-naphthols

Scheme 27. Chiral iron phosphate complex catalyzed asymmetric oxidative coupling reaction of β-naphthols

Scheme 28. Redox neutral cross-coupling reaction of 2-naphthols with azonaphthalene derivatives catalyzed by chiral phosphoric acid salt complex

Scheme 29. Oxidative coupling reaction of β-naphthols catalyzed by benzothiophene S-oxide

Scheme 30. Alkenylation reaction of β-naphthols

Scheme 31. Annulation reaction of β-naphthols with enals catalyzed by triazolium salt

Scheme 32. Copper-catalyzed asymmetric oxidative cross-coupling reaction of β-naphthols with aryl methyl ketones

Scheme 33. Silver-catalyzed cascade reaction of β-naphthols with 2-(phenylethynyl)cyclohex-2-en-1-ones

Scheme 34. Oxidative radical cyclization of β-naphthols with terminal alkynes catalyzed by boron trifluoride ether

Scheme 35. Bismuth trifluoromethanesulfate catalyzed [3＋2] cycloaddition reaction of D-A cyclopropanes with β-naphthols

Scheme 36. Silver trifluoromethanesulfonate catalyzed [3＋2] cycloaddition reaction of β-naphthols with aziridines

Scheme 37. Br?nsted acid-catalyzed annulation reaction of β-naphthols

Scheme 38. Iron catalyzed amination reaction of β-naphthols

Scheme 39. Direct ortho-selective amination and annulation of β-naphthols with hydrazines

Scheme 40. Coupling reaction of anilines with β-naphthols

Scheme 41. Scandium-catalyzed dearomatization and asymmetric amination reaction of β-naphthols with azodicarboxylates

Scheme 42. Rhodium-catalyzed aminative dearomatization of β-naphthols

Scheme 43. Copper-catalyzed asymmetric [4＋1] spirocyclization of α-bromo-β-naphthols with azoenes

Scheme 44. Coupling reaction of β-naphthols with anilines

Scheme 45. Coupling reaction of thiophenols with β-naphthols catalyzed by iodine

Scheme 46. Coupling reaction of thiophenols with β-naphthols catalyzed by piperidine

Scheme 47. Microwave-assisted coupling reaction of diaryl disulfides with β-naphthols

Scheme 48. Construction of sulfonated naphthols or aryl sulfides via coupling reaction of β-naphthols with sodium sulfinates

Scheme 49. Synthesis of sulfonated naphthols catalyzed by iron chloride

Scheme 50. Intermolecular dearomatization of β-naphthol derivatives with electrophilic disulfurating reagents catalyzed p-TsOH

Scheme 51. Base mediated selenation of β-naphthols

Scheme 52. Base-promoted regioselective selenization of β-naphthols

Scheme 53. Asymmetric hydroxylative dearomatization of β-naphthols catalyzed by scandium complex

Scheme 54. Dearomatic chlorination of β-naphthols catalyzed by cinchona derivatives

Scheme 55. Dearomatic halogenation of β-naphthols with N-halogenated succinimides

Scheme 56. PIFA-AlCl3 mediated ortho-chlorination of phenols and naphthalene ethers

Scheme 57. Iodination of phenols mediated by PhIO-NH4I

Scheme 58. Asymmetric dearomative fluorination of β-naphthols catalyzed by dicarboxylate

Scheme 59. Phosphorylation coupling reaction of β-naphthols at α-position

Scheme 60. Visible-light induced cross-coupling reaction of β-naphthols with diarylphosphine oxides

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β-萘酚α位反应的研究进展