芳香卤代物C—S偶联反应的研究进展

doi:10.6023/cjoc202303042

摘要/Abstract

含硫化合物在天然产物、药物、农药和材料中广泛存在, 具有多种生物活性或独特功能. C—S偶联反应是合成含硫化合物的重要方法, 是有机合成领域的研究热点之一. 随着对催化剂的深入开发和对含硫偶联反应物的不断扩展, 近年来涌现出大量的C—S偶联反应方法, 为含硫化合物的合成提供了便利. 芳香卤代烃是合成含硫化合物的主要底物, 通过设计不同的反应体系和含硫偶联反应物进行C—S偶联反应, 能够高效地合成硫酚、硫醚、二硫醚和砜等含硫化合物. 按照不同种类的含硫偶联反应物类型和催化剂种类(钯、铜和镍等)进行分类, 综述了近年来以芳香卤代烃为底物的C—S偶联反应, 并对代表性反应的机理做了简要说明和比较. 此外, 还对这一领域目前存在的问题和局限性进行简要分析, 并对未来发展方向提出展望.

关键词: C—S偶联反应, 芳香卤代物, 含硫化合物, 过渡金属催化剂

Sulfur-containing compounds are widely found in natural products, pharmaceuticals, pesticides, and materials, possessing a variety of biological activities or unique functions. C—S coupling reaction is an important method for the synthesis of sulfur-containing compounds and is one of the hot spots in the field of organic synthesis. With the in-depth development of catalysts and the continuous expansion of sulfur-containing coupling partners, a large number of C—S coupling reactions have emerged in recent years, which greatly facilitate the synthesis of sulfur-containing compounds. Aryl halides are the main kind of substrates for the synthesis of sulfur-containing compounds. C—S coupling reactions of aryl halides and sulfur-containing coupling partners can efficiently afford sulfur-containing compounds, such as thiophenols, thioethers, disulfides and sulfones in different well-designed reaction systems. In this review, the C—S coupling reactions with aryl halides as substrates are reviewed according to the different types of sulfur-containing coupling partners and catalysts (palladium, copper, nickel, and others). The mechanisms of representative reactions are briefly described and compared. In addition, a brief analysis of the current situations and limitations in this field is given, and a prospect for future development is put forward.

Key words: C—S coupling reaction, aryl halide, sulfur-containing compounds, transition-metal catalyst

引用此文

秦思凝. 芳香卤代物C—S偶联反应的研究进展[J]. 有机化学, 2023, 43(11): 3761-3783.

Sining Qin. Research Progress in C—S Coupling Reactions of Aryl Halides[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3761-3783.

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图/表 88

图式1. Pd2(dba)3催化的二芳基硫醚合成

Scheme 1. Pd2(dba)3 catalyzed synthesis of diaryl sulfide

图式2. Pd(OAc)2催化的二芳基硫醚合成

Scheme 2. Pd(OAc)2 catalyzed synthesis of diaryl sulfide

图式3. Pd/C催化的二芳基硫醚合成

Scheme 3. Pd/C catalyzed synthesis of diaryl sulfide

图式4. Pd(OAc)2催化的芳基硫醚合成

Scheme 4. Pd(OAc)2 catalyzed synthesis of aryl sulfide

图式5. Pd-PEPPSI-IPent催化的二芳基硫醚合成

Scheme 5. Pd-PEPPSI-IPent catalyzed synthesis of diaryl sulfide

图式6. CuI催化的芳基烷基硫醚的合成

Scheme 6. CuI catalyzed synthesis of aryl sulfide

图式7. 以儿茶酚紫为配体进行的铜催化C—S偶联反应

Scheme 7. Copper catalyzed C—S coupling reaction using catechol violet as ligand

图式8. Cu2O催化的芳基烷基硫醚的合成

Scheme 8. Cu2O catalyzed synthesis of aryl alkyl sulfides

图式9. 磁性含铜催化剂催化的二芳基硫醚合成

Scheme 9. Magnetic copper catalysts catalyzed synthesis of diaryl sulfides

图式10. CuO空心纳米球催化的C—S偶联反应

Scheme 10. C—S coupling reaction catalyzed by CuO hollow nanospheres

图式11. CuO催化的二芳基硫醚的合成

Scheme 11. CuO catalyzed synthesis of diaryl sulfide

图式12. CuO@ARF催化的二芳基硫醚合成

Scheme 12. CuO@ARF catalyzed synthesis of diaryl sulfide

图式13. CuI/DABCO催化的芳基硫醚合成

Scheme 13. CuI/DABCO catalyzed synthesis of aryl sulfide

图式14. 微波促进CuI的二芳基硫醚合成

Scheme 14. Microwave promoted CuI catalyzed synthesis of diaryl sulfide

图式15. 以草酸二酰胺为配体的铜催化C—S偶联反应

Scheme 15. Copper catalyzed C—S coupling reaciton using oxalic diamide as ligand

图式16. 铜催化的C—S/C—N偶联反应

Scheme 16. Copper catalyzed C—S/C—N coupling reaction

图式17. CuMoO4催化的C—S偶联反应

Scheme 17. CuMoO4 catalyzed C—S coupling reaction

图式18. CuMoO4纳米粒子催化的C—S偶联反应机理推测

Scheme 18. Proposed mechanism of CuMoO4 nanoparticles catalyzed C—S coupling reaction

图式19. CuI催化的无配体C—S偶联反应

Scheme 19. CuI catalyzed C—S coupling reaction without ligand

图式20. 微波促进的CuI催化的C—S偶联反应

Scheme 20. Microwave promoted CuI catalyzed C—S coupling reaction

图式21. Cu(II)配合物催化的C—S偶联反应

Scheme 21. Cu(II) complex catalyzed C—S coupling reaction

图式22. Ni配合物催化的C—S偶联反应

Scheme 22. Ni complex catalyzed C—S coupling reaction

图式23. Ni/Ir催化的光介导C—S偶联反应

Scheme 23. Ni/Ir catalyzed photoredox mediated C—S coupling reaction

图式24. NiCl2/NHC催化的C—S偶联反应

Scheme 24. NiCl2/NHC catalyzed C—S coupling reaction

图式25. NiCl2/NHC催化的C—S偶联反应机理推测

Scheme 25. Mechanism of NiCl2/NHC catalyzed C—S coupling reaction

图式26. Ni(II)复合物催化的C—S偶联反应

Scheme 26. Ni(II) complex catalyzed C—S coupling reaction

图式27. Ni(II)复合物催化的二芳基硫醚的合成

Scheme 27. Ni(II) complex catalyzed synthesis of diaryl sulfide

图式28. 电化学反应条件下芳香卤代物与硫酚的C—S偶联反应

Scheme 28. C—S coupling reaction of aryl halide and aryl thiols under electrochemical condition

图式29. Ni催化电化学合成芳基硫醚的反应机理推测

Scheme 29. Mechanism of Ni catalyzed synthesis of aryl sulfide under electrochemical condition

图式30. Ni(II)和Pd(II)复合物催化的硫醚合成

Scheme 30. Ni(II) and Pd(II) complexes catalyzed synthesis of sulfide

图式31. NiCl(allyl)(PMe2Ar')催化的C—S偶联反应

Scheme 31. NiCl(allyl)(PMe2Ar') catalyzed C—S coupling reaction

图式32. Ni(II)催化的C—S偶联反应

Scheme 32. Ni(II) catalyzed C—S coupling reaction

图式33. Ni(II)催化的C—S偶联反应机理预测

Scheme 33. Proposed mechanism of Ni(II) catalyzed C—S coupling reaction

图式34. 三氧化二铟纳米粒催化的C—S偶联反应

Scheme 34. Nano indium oxide catalyzed C—S coupling reaction

图式35. FeCl3催化的C—S偶联反应

Scheme 35. FeCl3 catalyzed C—S coupling reaction

图式36. Zr12-Ir-Ni催化的C—S偶联反应

Scheme 36. Zr12-Ir-Ni catalyzed C—S coupling reaction

图式37. Co(II)纳米催化剂催化的C—S偶联反应

Scheme 37. Co(II) nanocatalyst catalyzed C—S coupling reaction

图式38. Fe3O4(Al)-NH2-Co(II)纳米颗粒催化合成芳基硫醚的反应机理推测

Scheme 38. Speculation on the reaction mechanism of aryl sulfide synthesis catalyzed by Fe3O4(Al)-NH2-CoII nanoparticles

图式39. 次硫酸氢钠甲醛催化的C—S偶联反应

Scheme 39. Rongalite catalyzed C—S coupling reaction

图式40. 吡啶-硼烷复合物促进的C—S偶联反应

Scheme 40. Pyridine-boryl complexes promoted C—S coupling reaction

图式41. 微波促进下芳香卤代烃和苄基卤代物与磺酰肼的C—S偶联反应

Scheme 41. Microwave promoted C—S coupling reaction of aryl/benzyl halide and sulfonyl hydrazides

图式42. 微波条件下镍复合物催化的C—S偶联反应

Scheme 42. Ni complex catalyzed C—S coupling reaction under microwave irradiation

图式43. 芳香碘代物和芳基磺酰氯的C—S偶联反应

Scheme 43. C—S coupling reaction of aryl iodide and aryl sulfonyl chloride

图式44. 以HEH为光催化剂的C—S偶联反应

Scheme 44. Photocatalyzed C—S coupling reaction with HEH as catalyst

图式45. Cu(CH3CN)4PF6催化的二芳基砜的合成

Scheme 45. Cu(CH3CN)4PF6 catalyzed synthesis of diaryl sulfone

图式46. Cl-TXO/溴化镍催化的二芳基砜的光合成

Scheme 46. Cl-TXO/NiBr2 catalyzed photo-synthesis of diaryl sulfone

图式47. Cl-TXO/溴化镍催化的二芳基砜的光合成反应机理推测

Scheme 47. Proposed reaction mechanism of Cl-TXO/NiBr2 catalyzed photo-synthesis of diaryl sulfone

图式48. Ni(py)4Cl2催化的成对电解反应合成芳基硫醚类化合物

Scheme 48. Ni(py)4Cl2 catalyzed paired electrolysis for the synthesis of aryl sulfides

图式49. 二芳基砜或二芳基硫醚的选择性电化学合成

Scheme 49. Electrochemistry enabled selective synthesis of diaryl sulfones and diaryl sulfides

图式50. 铱/镍双催化的C—S偶联反应

Scheme 50. Ir/Ni dual-catalyzed C—S coupling reaction

图式51. 硫代磺酸酯为硫源的C—S偶联反应

Scheme 51. C—S coupling reaction using thiosulfonate as sulfur source

图式52. 以硫脲为硫源合成芳基烷基醚

Scheme 52. Synthesis of aryl alkyl sulfide using thiourea as sulfur source

图式53. 以硫脲为硫源合成对称芳基硫醚

Scheme 53. Synthesis of symmetrical diaryl sulfide using thiourea as sulfur source

图式54. 以PEG200为溶剂合成二芳基硫醚

Scheme 54. Synthesis of symmetric diaryl sulfide using PEG200 as solvent

图式55. C—S交叉偶联反应制备S-芳基异硫脲盐

Scheme 55. Preparation of S-aryl isothiouronium via C—S coupling

图式56. 纳米催化剂CoFe2O4催化的芳基苄基硫醚合成

Scheme 56. Nonocatalyst CoFe2O4 catalyzed synthesis of aryl benzyl sulfide

图式57. 二硫代四氟苯的合成

Scheme 57. Synthesis of dithiotetrafluorobenzene

图式58. 无金属催化下合成二硫代四氟苯的反应机理

Scheme 58. Mechanism of the synthesis of dithiotetrafluorobenzene without metal catalyst

图式59. [Fe3O4@SiO2/2-氨基吡啶-Pd(II)]催化的C—S偶联反应

Scheme 59. [Fe3O4@SiO2/2-aminopyridine-Pd(II)] catalyzed C—S coupling reaction

图式60. N-硫基邻苯二甲酰亚胺为硫源的C—S偶联反应

Scheme 60. C—S coupling reaction using N-thiophthalimide as sulfur source

图式61. 铜催化二苯基硫代氨基甲酸酯的合成

Scheme 61. Copper catalyzed synthesis of diphenylcarbamothioate

图式62. S-苯基硫代乙酸酯为硫源合成二芳基硫醚

Scheme 62. Synthesis of diaryl sulfide using aryl thioacetates as sulfur source

图式63. 芳基碘代物与硫代苯甲酸的C—S偶联反应

Scheme 63. C—S coupling reaction of aryl iodides and thiobenzoic acid

图式64. 钯催化的S-芳基硫代乙酸酯的合成

Scheme 64. Palladium catalyzed synthesis of S-aryl thioacetates

图式65. 以硫代乙酸钾为硫源合成二芳基硫醚

Scheme 65. Synthesis of diaryl sulfide using potassium thioacetate as sulfur source

图式66. 以硫代乙酸酯为硫源合成硫醚

Scheme 66. Synthesis of sulfide using thioacetate as sulfur source

图式67. 以5-甲基-1,3,4-噁二唑-2硫醇钾盐为硫源的C—S偶联反应

Scheme 67. C—S coupling reaction using 5-methyl-3H- 1,3,4-oxadiazole-2-thione as sulfur source

图式68. 以乙基黄原酸钾为硫源的C—S偶联反应

Scheme 68. C—S coupling reaction using potassium ethylxanthate as sulfur source

图式69. 硫代乙酰胺作为硫源合成对称二芳基硫醚

Scheme 69. Synthesis of symmetrical diaryl sulfide using thioacetamide as sulfur source

图式70. 卤代芳烃与苯并咪唑磺酰胺硫醚的C—S偶联反应

Scheme 70. C—S coupling reaction of aryl halide and IMDN- SO2R

图式71. 卤代芳烃与苯并咪唑磺酰胺硫醚的C—S偶联反应机理推测

Scheme 71. Possible mechanism of C—S coupling reaction of aryl halide and IMDN-SO2R

图式72. 芳基硫乙酸与芳基溴代物的C—S偶联反应

Scheme 72. C—S coupling reaction of phenylthioacetic acid and aryl bromide

图式73. 对称二芳基硫醚与二芳基二硫醚的合成

Scheme 73. Synthesis of symmetric diaryl sulfide and diaryl disulfide

图式74. 水溶液中合成二芳基二硫醚

Scheme 74. Synthesis of diaryl disulfide in water

图式75. 芳基卤代物与三苯基氯化锡的C—S偶联反应

Scheme 75. C—S coupling reaction of aryl halide and triphenyltin chloride

图式76. 二芳硫基咪唑并[1,2-α]吡啶类化合物的合成

Scheme 76. Synthesis of disulfenylated imidazo[1,2-a]pyridine

图式77. 水溶性胶束介导的C—S偶联反应

Scheme 77. Micelle-mediated C—S coupling reaction

图式78. 2-芳基苯并噻唑的合成

Scheme 78. Synthesis of 2-aryl benzothiazole

图式79. Cu催化合成2-芳基苯并噻唑的反应机理

Scheme 79. Reaction mechanism of Cu catalyzed synthesis of 2-aryl benzothiazole

图式80. 光诱发的选择性C—S键构建

Scheme 80. Photo-induced selective construction of C—S bond

图式81. (Z)-3-苯硫基丙烯酸类化合物的合成

Scheme 81. Synthesis of (Z)-3-phenylthioacrylic acid

图式82. 对称二芳基硫醚的合成

Scheme 82. Synthesis of symmetrical diaryl sulfide

图式83. 以NaS2O3为硫源合成二芳基硫醚

Scheme 83. Synthesis of diaryl sulfide using NaS2O3 as sulfur source

图式84. 芳基烯基硫醚的合成

Scheme 84. Synthesis of aryl alkenyl thioether

图式85. 芳基烯基硫醚的合成反应机理推测

Scheme 85. Predicted reaction mechanism of synthesis of aryl alkenyl thioether

图式86. S-芳基二硫代氨基甲酸酯的合成

Scheme 86. Synthesis of S-aryl dithiocarbamates

图式87. β-羟基硫醚的合成

Scheme 87. Synthesis of β-hydroxysulfides

图式88. 以KSCN为硫源合成对称二芳基硫醚

Scheme 88. Synthesis of symmetrical diaryl sulfide using KSCN as sulfur source

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