Recent Progress on Arylation with Aryne through Three-Component Reaction

doi:10.6023/cjoc202206006

Abstract

The three component reaction has the advantages of simple operation and efficient reaction, in line with the principles of atomic economy and green environmental protection. At present, the arylation without transition metal catalyst is mainly divided into three types of as following: (1) the direct arylation, (2) the insertion of aryne into σ-bond or π-bond, and (3) the three-component reactions involving aryne. Compared with the direct arylation and the insertion of aryne into σ-bond or π-bond, the mechanism of three component reactions involving aryne is still unclear, and the published reviews are still lacking. In order to facilitate the scientific researchers to consult and understand the three-component reaction involved in aryne, the progresses in the three-component reaction involving aryne in recent years are reviewed.

Key words: aryne, three component reaction, carbon and heteroatom, arylation

Cite this article

Dongping Chen, Chunhong Yang, Ming Li, Guoxiao Zhao, Wenpeng Wang, Xicun Wang, Zhengjun Quan. Recent Progress on Arylation with Aryne through Three-Component Reaction[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 503-525.

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Fig. & Tab. 91

Scheme 1. Kobayashi benzyne precursor

Scheme 2. Three-component reaction mechanism involving aryne

Scheme 3. Three-component reaction of aryne, methoxyphosphine compounds and carbon dioxide

Scheme 4. Three-component reaction of aromatic alkyne, trivalent phosphorus and aldehyde

Scheme 5. Three-component reaction of aryne, triarylphosphine and activated ketones

Scheme 6. Three-component reaction of aryne, tertiary phosphine and carbon dioxide

Scheme 7. Three-component reaction of aryne, phosphite ester and halide

Scheme 8. Three-component reaction of aryne, phosphite ester and ketones

Scheme 9. Three-component reaction of aryne, DMSO and α-bromocarbonyl compounds

Scheme 10. Three-component reaction of aryne, DMSO and activated alkyne

Scheme 11. Three-component reaction of aryne, sulfoxide and carbonyl electrophiles (N-methylisancin and activated aromatic aldehyde)

Scheme 12. Three-component reaction of aryne, aryl allyl sulfoxide and bromoalkane

Scheme 13. Three-component reaction of aryne, thiourea and halogenated ester

Scheme 14. Three-component reaction of aryne, activated olefin and dimethyl sulfoxide

Scheme 15. Three-component reaction of aryne, thioether and indigo

Scheme 16. Three component reaction of aromatic alkyne, phenylthiosulfate and phenylacetylene

Scheme 17. Three-component reaction of aryne, trifluoromethylthio silver and 2-iodophenylacetylene

Scheme 18. Three-component reaction of aryne, sulfur heterocyclic compound and nucleophile

Scheme 19. Three-component reaction of aryne, sulfur heterocyclic compound and 2,3-dimethylindole

Scheme 20. Three-component reaction of aryne, sulfur heterocyclic compound and silylation

Scheme 21. Three-component reaction of benzyne, tertiary amines and 2-phenylth-ioisoindoline-1,3-dione

Scheme 22. Three-component reaction of aromatic alkyne, thiophenol and aldehyde

Scheme 23. Aromatic alkyne, sodium sulfite and aldehyde three-component reaction

Scheme 24. Three-component reaction of aryne, carbon disulfide and secondary amine

Scheme 25. Three-component reaction of aryne, trifluoromethyl phenylthiomate and halo-substituted reagents

Scheme 26. Three-component reaction of aryne, epoxy compounds and chloroform

Scheme 27. Three-component reaction of aryne, epoxy compounds and alkynyl bromide

Scheme 28. Three-component reaction of aryne, fatty alcohol and tetrahydrofuran

Scheme 29. Three-component reaction of aryne, hydroxylamine and butylene dicarboxylate

Scheme 30. Three-component reaction of benzyne, benzoylnitrile and DMF

Scheme 31. Three-component reaction of benzyne, diaryliodonium salt and DMF

Scheme 32. Three-component reaction of benzyne, arylsulfonyl chloride and DMF

Scheme 33. Three-component reaction of aromatic, N,S-enone acetal and DMF

Scheme 34. Three-component reaction of aryne, 2-bromoacetyl- benzene and DMF

Scheme 35. Three-component reaction of aryne, allyl bromide and DMF

Scheme 36. Three-component reaction of aryne, TFBz and halide

Scheme 37. Three-component reaction of aryne, TFMS and C4F9I

Scheme 38. Three-component reaction of aryne, formamide and diarylphosphine oxide compounds

Scheme 39. Three-component reaction of aryne, imine and CO2

Scheme 40. Three-component reaction of aryne, secondary amine and CO2

Scheme 41. Three-component reaction of aryne, aminosilane and aldehyde or sulfonimide

Scheme 42. Three-component reactions of arynes, N-hetero- cyclic aromatic hydrocarbon and terminal alkyne or ketone

Scheme 43. Three-component reaction of aryne, azetidine and acetonitrile

Scheme 44. Three-component reaction of aryne, azacyclopropane containing 2-carbonyl substituent and TBAF hydrate

Scheme 45. Three-component reaction of aryne, N-substituted azetidine and water

Scheme 46. Three-component reaction of aryne, carboxylic acid and azetidine or azetidine

Scheme 47. Three-component reaction of aryne, electron deficiency N-substituted azetidylene and aldehyde

Scheme 48. Three-component reactions of aromatic alkynes, azetate rings and carbonyl indole

Scheme 49. Three-component reaction of aryne, quinoline and ketone

Scheme 50. The formation pathway of pyridine carbine in three-component reaction of aryne, N-heterocyclic and carbonyl indole

Scheme 51. Three-component reaction of aryne, carbodiimide and terminal alkyne or halogenate

Scheme 52. Three-component reaction of aryne, aromatic tertiary amines and aldehyde ketone

Scheme 53. Three-component reaction of aryne, electron-defi- ciency aza aromatic hydrocarbon and dialkyl phosphate

Scheme 54. Three-component reaction of aromatic hydrocarbons, aromatic tertiary amine and carbon dioxide

Scheme 55. Three-component reaction of aryne, aldehyde and substituted indole (n=1) or tetrahydroquinoline (n=2)

Scheme 56. Three-component reaction of aryne, TsNHNH2 and α-bromoaryl ketone

Scheme 57. Three-component reaction of aryne, benzothiophene and 1,2-dichloroethane or acetonitrile

Scheme 58. Three-component reaction of aromatic, N-hetero- aromatics (pyridine, quinoline, isoquinoline) and nitrile compounds

Scheme 59. Three-component reaction of aryne, N-hetero aromatic and chloroform

Scheme 60. Three-component reaction of aryne, electron-defi- ciency heteroaryl compound and carbon tetrachloride

Scheme 61. Three-component reaction of aryne, imine and carbon nucleophile

Scheme 62. Three-component reaction of aryne, acetonitrile and isoquinoline or dihydrogen analogues of pyridine

Scheme 63. Three-component reaction of aryne, α-diazo-β- carbonylphosphonate and conjugated olefins

Scheme 64. Three-component reaction of aryne, enantiomer- rich tertiary benzylamine and nucleophile

Scheme 65. Three-component reaction of aryne, DABCO, acetonitrile and nucleophile

Scheme 66. Three-component reaction of aryne, electron-defi- ciency heteroaryl compound and carbon tetrachloride

Scheme 67. Three-component reaction of aryne, oxazoliprine and chloroform

Scheme 68. Three-component reaction of benzene, tertiary amines and organic halide

Scheme 69. Three-component reaction of benzyne, phenyltertiary amine and arylselenium or seleniumbromide

Scheme 70. Three-component reaction of aryne, sodium nitrite and aldehyde

Scheme 71. Three-component reaction of aryne, secondary amine and sulfonyl fluoride

Scheme 72. Three-component reaction of benzyne, isonitrile and aldehyde

Scheme 73. Three-component reaction of aromatic alkyne, isocyanide and aldehyde

Scheme 74. Three-component reaction of aryne, pyridine and 2-bromoacetylacetone

Scheme 75. Three-component reaction of aryne, isonitrile and terminal alkyne

Scheme 76. Three-component reaction of benzyne, isonitrile and 3-bromopropyne or 3-acetoxypropyne

Scheme 77. Three-component reaction of benzyne, isonitrile and ester

Scheme 78. Three-component reaction of benzyne, isonitrile and activated alkyne

Scheme 79. Three-component reaction of benzyne, isonitrile and bromide

Scheme 80. Three-component reaction of aryne, isocyanide and carbon dioxide or water

Scheme 81. Three-component reaction of aromatic alkynes, alcohol compounds and activated olefins or carbodiimides

Scheme 82. Three-component reaction of benzyne, allyl bromide and carbon dioxide

Scheme 83. Three-component reaction of aryne, 1,3-dicarbonyl compound and alkynate

Scheme 84. Three-component reaction of aryne, β-keto sulfone and electron-deficiency olefin

Scheme 85. Three-component reaction of aryne, α-cyanoace- tone (R2=CN) or 1,3-diketone (R2=COAr) and alkynate

Scheme 86. Three-component reaction of aryne, CsF and C4F9I

Scheme 87. Aromatic insertion reaction of aromathyne, tetra- aryldiphosphine and S8

Scheme 88. Four-component reaction of aryne, cyclic ether, CO2 and amine

Scheme 89. Three-component reaction of aryne, potassium iodide and aldehyde

Scheme 90. Four-component reaction of aryne, inorganic salt, carbon dioxide and chlorocarbon

Scheme 91. Aromatic nucleophilic substitution/dearonylation reaction initiated by aryne

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