β-萘酚α位反应的研究进展

doi:10.6023/cjoc202207015

摘要/Abstract

β-萘酚是有机合成中一种重要的合成子, 其α位化学性质活泼, 可参与多种化学反应, 受到了化学家的广泛关注. β-萘酚的α位可以发生多种化学转化, 如烷基化、芳基化、环化、胺化和卤化等, 利用这些化学反应可以构建结构多样化且具有不同生物活性的萘酚衍生物. 这些萘酚衍生物既可以作为天然活性药物的关键骨架, 也可以用于制备化学合成中的重要中间体. 基于近年来β-萘酚α位的化学反应层出不穷, 主要从β-萘酚α位碳-碳键和碳-杂键(C-N, C-O, C-X, C-S, C-P)的构建来对β-萘酚α位的相关反应进行了综述.

关键词: β-萘酚, α位, 碳-碳键, 碳-杂键

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

引用此文

刘静, 陈锦涛, 刘婷婷, 刘佳, 曾要富. β-萘酚α位反应的研究进展[J]. 有机化学, 2023, 43(2): 379-410.

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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图/表 60

图式1. β-萘酚与α-氨基砜的Friedel-Crafts反应

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

图式2. β-萘酚与烯胺的Friedel-Crafts烷基化反应

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

图式3. β-萘酚与二芳基甲醇的Friedel-Crafts型脱水烷基化反应

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

图式4. β-萘酚与氨基环丙烷的不对称Friedel-Crafts反应

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

图式5. 双核锌配合物催化β-萘酚与亚胺的aza-Friedel-Crafts反应

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

图式6. β-萘酚与吡唑啉酮亚胺类化合物的不对称aza-Friedel-Crafts/N,O-缩醛化反应

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

图式7. β-萘酚与苯并噻唑胺的aza-Friedel-Crafts反应

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

图式8. TCCA催化的三组分反应合成酰胺烷基萘酚

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

图式9. 三氟乙酸铁催化的萘酚、甲醛和苯胺的多组分反应

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

图式10. β-萘酚与芳烃磺酰基烷基吲哚的Michael加成反应

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

图式11. 光催化的β-萘酚与甘氨酸衍生物的氧化脱氢偶联反应

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

图式12. 2-氯环戊酮或2-氯环己酮对β-萘酚的去芳构化反应

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

图式13. β-萘酚的去芳构化烯丙基化反应

Scheme 13. Dearomatic allylation reaction of β-naphthols

图式14. 铑催化的β-萘酚与芳基乙烯基甲醇的去芳构化不对称烯丙基反应

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

图式15. 钯催化β-萘酚与偕二氟环丙烷的烯丙基烷基化去芳构化反应

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

图式16. 钯催化β-萘酚的不对称多米诺Heck/脱芳构化反应

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

图式17. 金催化β-萘酚与炔基的分子内去芳构化氢烷基化反应

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

图式18. 铜催化的β-萘酚去芳构化立体选择性的炔丙基反应

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

图式19. 二芳基碘鎓盐对β-萘酚的芳基化反应

Scheme 19. Arylation of β-naphthols with diaryliodonium salts

图式20. 富电子苯酚和β-萘酚的氧化交叉偶联

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

图式21. 手性磷酸催化的β-萘酚与醌衍生物的不对称芳基化反应

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

图式22. Br?nsted酸催化的醌单缩醛与β-萘酚直接芳基化反应

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

图式23. 奎宁催化β-萘酚与卤代醌的偶联反应

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

图式24. 四聚肽催化的β-萘酚与醌衍生物的偶联反应

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

图式25. Br?nsted酸催化β-萘酚与吖嗪类化合物的杂芳基化反应

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

图式26. 可见光催化β-萘酚芳基化反应

Scheme 26. Photocatalytic arylation reaction of β-naphthols

图式27. 手性磷酸铁配合物催化的β-萘酚的不对称氧化偶联反应

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

图式28. 手性磷酸盐配合物催化的2-萘酚与偶氮萘衍生物氧化还原中性交叉偶联反应

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

图式29. 苯并噻吩硫氧化物催化的β-萘酚的氧化偶联反应

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

图式30. β-萘酚的烯基化反应

Scheme 30. Alkenylation reaction of β-naphthols

图式31. 三唑鎓盐催化的β-萘酚与烯醛的环化反应

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

图式32. 铜催化的β-萘酚与芳基甲基酮不对称氧化交叉偶联反应

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

图式33. 银催化的β-萘酚与2-(苯乙炔基)环己-2-烯-1-酮的串联反应

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

图式34. 三氟化硼乙醚催化的β-萘酚和末端炔烃氧化自由基环化反应

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

图式35. 三氟甲磺酸铋催化的D-A环丙烷与β-萘酚的[3＋2]环加成反应

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

图式36. 三氟甲磺酸银催化的β-萘酚与氮丙啶的[3＋2]环加成反应

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

图式37. Br?nsted酸催化的β-萘酚的环加成反应

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

图式38. 铁催化的β-萘酚的胺化反应

Scheme 38. Iron catalyzed amination reaction of β-naphthols

图式39. 肼对β-萘酚的直接选择性邻位胺化和环化反应

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

图式40. 苯胺与β-萘酚的偶联反应

Scheme 40. Coupling reaction of anilines with β-naphthols

图式41. 钪催化β-萘酚与偶氮二羧酸盐的去芳构化不对称胺化反应

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

图式42. 铑催化β-萘酚的去芳构化胺化反应

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

图式43. 铜催化α-溴-β-萘酚与偶氮烯的不对称[4＋1]螺环化反应

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

图式44. β-萘酚与苯胺的偶联反应

Scheme 44. Coupling reaction of β-naphthols with anilines

图式45. 碘催化苯硫酚与β-萘酚的偶联反应

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

图式46. 哌啶催化苯硫酚与β-萘酚的偶联反应

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

图式47. 微波辅助二芳基二硫化合物与β-萘酚的偶联反应

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

图式48. β-萘酚与亚磺酸钠构建磺化萘酚或芳基硫醚的偶联反应

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

图式49. 氯化铁催化的磺化萘酚的合成

Scheme 49. Synthesis of sulfonated naphthols catalyzed by iron chloride

图式50. 对甲苯磺酸催化β-萘酚衍生物与亲电二硫代试剂的分子间脱芳构化反应

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

图式51. 碱介导的β-萘酚的硒化反应

Scheme 51. Base mediated selenation of β-naphthols

图式52. 碱促进的β-萘酚的区域选择性硒化反应

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

图式53. 钪配合物催化的β-萘酚去芳构化不对称羟基化反应

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

图式54. 金鸡碱衍生物催化β-萘酚的去芳构化氯化反应

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

图式55. N-卤代琥珀酰亚胺对β-萘酚的去芳构化卤化反应

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

图式56. PIFA-AlCl3介导的酚类和萘醚的邻位氯化反应

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

图式57. PhIO-NH4I介导的酚类的碘化反应

Scheme 57. Iodination of phenols mediated by PhIO-NH4I

图式58. 二羧酸盐催化β-萘酚的不对称去芳构化氟化反应

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

图式59. β-萘酚α位的膦酰化偶联反应

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

图式60. 可见光诱导的β-萘酚与二芳基膦氧化合物的交叉偶联反应

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

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