Research Progress in the Cyclization Reactions with Propargyl Alcohols

doi:10.6023/cjoc202203037

Abstract

Propargyl alcohols as a classical bifunctional group compounds possess alcohol hydroxyl group and carbon-carbon triple bond. Due to their special structure, they show unique reaction characteristics, and are employed in reactions via activating its alcoholic hydroxyl group or triple bond. The most typical reaction for propargyl alcohols is various cyclization reactions with different compounds to assemble a richer variety of cyclized compounds such as cyclopentene, pyrrole, furan, cyclic carbonate, pyran, pyridine and azepine cyclic compounds. The recent research progress in the cyclization reaction of propargyl alcohols with various compounds, including [3+2], [2+3], [3+3], [4+2], [2+4], [4+1], [3+4] and other types of cyclization reactions, is summarized.

Key words: propargyl alcohol, bifunctional group, alcohol hydroxyl, carbon-carbon triple bond, cascade reaction, cyclization

Cite this article

Xiaozheng Zhao, Qinqin Ling, Guiyan Cao, Xing Huo, Xiaolong Zhao, Yingpeng Su. Research Progress in the Cyclization Reactions with Propargyl Alcohols[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2605-2639.

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Fig. & Tab. 71

Scheme 1. Cyclization reactions involving propargyl alcohol

Scheme 2. Pre-activation of the triple bond induced reaction mode

Scheme 3. Pre-activation of the hydroxyl induced reaction mode

Scheme 4. BF3•Et2O-catalyzed cascade cyclization reaction of propargyl alcohol and ketene dithioacetal

Scheme 5. Silver-catalyzed cascade cyclization reaction of propargyl alcohol and indole

Scheme 6. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and azide

Scheme 7. Chiral phosphoric acid-catalyzed asymmetric cascade cyclization reaction of propargyl alcohol and indole

Scheme 8. t-BuOK-catalyzed cascade cyclization reaction of propargyl alcohol and hydrazine

Scheme 9. DABCO-catalyzed cascade cyclization reaction of propargyl alcohol and methyl 2-perfluoroalkynoate

Scheme 10. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and alkyne

Scheme 11. Et3N-mediated cascade cyclization reaction of propargyl alcohol and aryl carboxylic acid

Scheme 12. t-BuOI-promoted cascade cyclization reaction of propargyl alcohol and CO2

Scheme 13. Silver-catalyzed cascade cyclization reaction of propargyl alcohol and CO2

Scheme 14. Electro-catalyzed cascade cyclization reaction of propargyl alcohol and CO2

Scheme 15. MTBD-catalyzed cascade cyclization reaction of propargyl alcohol and CO2

Scheme 16. Silver-catalyzed cascade cyclization reaction of propargyl alcohol and CO2

Scheme 17. Energy diagram of the carboxylation cyclization of propargyl alcohol with CO2 catalyzed by Ag(I)-DavePhos

Scheme 18. NaOtP-promoted cascade cyclization reaction of propargyl alcohol and CO2

Scheme 19. Calcium-catalyzed cascade cyclization reaction of propargyl alcohol and aryl olefin

Scheme 20. Iron-catalyzed cascade cyclization reaction of propargyl alcohol and phenol

Scheme 21. Calcium-catalyzed cascade cyclization reaction of propargyl alcohol and 2-naphthol

Scheme 22. Bu4NPF6-mediated cascade cyclization reaction of propargyl alcohol and naphthol

Scheme 23. Zinc-catalyzed cascade cyclization reaction of propargyl alcohol and aminocarbazole

Scheme 24. Ruthenium-catalyzed cascade cyclization reaction of propargyl alcohol and N-pyridineaniline

Scheme 25. Aluminium-catalyzed cascade cyclization reaction of propargyl alcohol and aminopyrimidine

Scheme 26. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and N-nitrosoaniline

Scheme 27. Ytterbium-catalyzed cascade cyclization reaction of propargyl alcohol and 2-indolecarbinol or benzyl alcohol

Scheme 28. Calcium-catalyzed cascade cyclization reaction of propargyl alcohol and cycloenol

Scheme 29. TFA-mediated cascade cyclization reaction of propargyl alcohol and 1,3-dione

Scheme 30. BF3•Et2O-promoted cascade cyclization reaction of propargyl alcohol and 3-(1,3-dithiothiophene) acrylamide or carboxylic acid

Scheme 31. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and diazonaphthoquinone

Scheme 32. BF3•Et2O-catalyzed cascade cyclization reaction of propargyl alcohol and enaminone

Scheme 33. BF3•Et2O-promoted cascade cyclization reaction of propargyl alcohol and primary amine and methyl 2-butynedicarboxylate

Scheme 34. Palladium/copper-catalyzed cascade cyclization reaction of propargyl alcohol and 1-amino-2-bromopyrrole

Scheme 35. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and aziridine

Scheme 36. Iron-catalyzed cascade cyclization reaction of propargyl alcohol and aromatic amine

Scheme 37. Iodine-mediated cascade cyclization reaction of propargyl alcohol and aryl azides

Scheme 38. Silver-catalyzed cascade cyclization reaction of propargyl alcohol and 3-methyleneisoindol-1-one

Scheme 39. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and imine

Scheme 40. Dual-catalyzed cascade cyclization reaction of propargyl alcohol and 2-hydroxynitrostyrene.

Scheme 41. Ruthenium-catalyzed cascade cyclization reaction of propargyl alcohol and benzyl imide

Scheme 42. Gibb's free energy profile in DCM solvent

Scheme 43. Ruthenium and base-catalyzed two-step cyclization reaction of propargyl alcohol and N-p-toluenesulfonylbenzamide

Scheme 44. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and oxime

Scheme 45. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and 3-arylisoxazolone

Scheme 46. Rhodium-catalyzed cascade cyclization reaction of propargyl alcohol and benzoic acid

Scheme 47. Copper-catalyzed cascade cyclization reaction of propargyl alcohol and nitrile

Scheme 48. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and pyridine N-oxide

Scheme 49. Calculated transition states for the two conceivable shift reactions and the activation barriers

Scheme 50. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and water

Scheme 51. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and α-diazoester

Scheme 52. Palladium-catalyzed cascade cyclization reaction of propargyl alcohol and α-diazoester

Scheme 53. Palladium-catalyzed cascade cyclization reaction of propargyl alcohol and TFBen

Scheme 54. Palladium-catalyzed cascade cyclization reaction of propargyl alcohol and aryl triflate

Scheme 55. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and hydroxylamine

Scheme 56. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and o-phenylenediamine

Scheme 57. Yttrium-catalyzed cascade cyclization reaction of propargyl alcohol and 2-azidomethyl-1H-indole

Scheme 58. Copper-catalyzed cascade cyclization reaction of propargyl alcohol and indole-2-carboxylic acid or amide

Scheme 59. p-TSA-catalyzed cascade cyclization reaction of propargyl alcohol and indole-3-amide

Scheme 60. BF3•Et2O-promoted cascade cyclization reaction of propargyl alcohol and secondary amine and 2-butynedicarboxylates

Scheme 61. 2,2',2''-Terpyridine-catalyzed cascade cyclization reaction of propargyl alcohol and primary amines and CO2

Scheme 62. Gold/copper-catalyzed cascade cyclization reaction of propargyl alcohol and pyridyl homopropargyl alcohol

Scheme 63. Ruthenium-catalyzed cascade cyclization reaction of propargyl alcohol and arylazocarbimide

Scheme 64. Gold-catalyzed intro-molecular cyclization of propargyl alcohol

Scheme 65. Gold-catalyzed cascade cyclization reaction of propargyl alcohol and 1,3,5-trimethylbenzene

Scheme 66. Gold-catalyzed cascade cyclization reaction of propargyl alcohol

Scheme 67. Palladium-catalyzed cascade cyclization-amination of propargyl alcohol and amine

Scheme 68. MsOH-promoted cascade cyclization reaction of propargyl alcohol

Scheme 69. Silver-catalyzed cascade cyclization reaction of propargyl alcohol

Scheme 70. p-TsOH-catalyzed or iodine-mediated cascade cyclization reaction of propargyl alcohol

Scheme 71. Copper-catalyzed cascade cyclization reaction of propargyl alcohol and diarylphosphine oxide

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