Research Progress in C—S Coupling Reactions of Aryl Halides

doi:10.6023/cjoc202303042

Abstract

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

Cite this article

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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Fig. & Tab. 88

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

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

Scheme 3. Pd/C catalyzed synthesis of diaryl sulfide

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

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

Scheme 6. CuI catalyzed synthesis of aryl sulfide

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

Scheme 8. Cu2O catalyzed synthesis of aryl alkyl sulfides

Scheme 9. Magnetic copper catalysts catalyzed synthesis of diaryl sulfides

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

Scheme 11. CuO catalyzed synthesis of diaryl sulfide

Scheme 12. CuO@ARF catalyzed synthesis of diaryl sulfide

Scheme 13. CuI/DABCO catalyzed synthesis of aryl sulfide

Scheme 14. Microwave promoted CuI catalyzed synthesis of diaryl sulfide

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

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

Scheme 17. CuMoO4 catalyzed C—S coupling reaction

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

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

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

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

Scheme 22. Ni complex catalyzed C—S coupling reaction

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 35. FeCl3 catalyzed C—S coupling reaction

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

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

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

Scheme 39. Rongalite catalyzed C—S coupling reaction

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 56. Nonocatalyst CoFe2O4 catalyzed synthesis of aryl benzyl sulfide

Scheme 57. Synthesis of dithiotetrafluorobenzene

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

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

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

Scheme 61. Copper catalyzed synthesis of diphenylcarbamothioate

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

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

Scheme 64. Palladium catalyzed synthesis of S-aryl thioacetates

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

Scheme 66. Synthesis of sulfide using thioacetate as sulfur source

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

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

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

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

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

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

Scheme 73. Synthesis of symmetric diaryl sulfide and diaryl disulfide

Scheme 74. Synthesis of diaryl disulfide in water

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

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

Scheme 77. Micelle-mediated C—S coupling reaction

Scheme 78. Synthesis of 2-aryl benzothiazole

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

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

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

Scheme 82. Synthesis of symmetrical diaryl sulfide

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

Scheme 84. Synthesis of aryl alkenyl thioether

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

Scheme 86. Synthesis of S-aryl dithiocarbamates

Scheme 87. Synthesis of β-hydroxysulfides

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

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芳香卤代物C—S偶联反应的研究进展