Research Progress of Transition Metal Catalyzed Synthesis of 1,3- Conjugated Diene Compounds from Alkenes and Alkynes

doi:10.6023/cjoc202210017

Abstract

1,3-Conjugated dienes are key structural units of many natural products and drugs. Conjugated alkenes also play a central role in organic synthesis and materials science due to their special chemical properties. At present, the synthesis of 1,3-conjugated diene is mainly achieved by transition metal catalysis, and researchers have constructed a series of 1,3-diene skeletons through this method, which enriches the structural diversity of conjugated diene compounds and extends the application range of diene compounds. The synthesis of 1,3-diene is reviewed by classification based on the different types of transition metal catalysts, and its development prospects are prospected.

Key words: transition metal catalysis, 1,3-conjugated diene, organic synthesis, application

Cite this article

Guangli Xu, Jing Xu, Haidong Xu, Xiang Cui, Xingzhong Shu. Research Progress of Transition Metal Catalyzed Synthesis of 1,3- Conjugated Diene Compounds from Alkenes and Alkynes[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1899-1933.

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Fig. & Tab. 62

Figure 1. Conjugated alkenes and polyene natural products

Scheme 1. Palladium catalyzed synthesis of 1,3-diene from enyl sulfonate and enone

Scheme 2. Palladium catalyzed synthesis of 1,3-diene from enyl sulfonate and alkyne

Scheme 3. Palladium catalyzed the synthesis of 1,3-diene from enyl sulfonate and alkene

Scheme 4. Palladium catalyzed synthesis of 1,3-diene from enyl sulfonate and alkene

Scheme 5. Palladium catalyzed synthesis of 1,3-diene from cinnamic acid and enyl bromide

Scheme 6. Palladium catalyzed synthesis of 1,3-diene from alkenyl halogenated hydrocarbons and organolithium reagents

Scheme 7. Palladium catalyzed synthesis of 1,3-diene from enyl bromide and N-sulfonylhydrazones

Scheme 8. Palladium catalyzed synthesis of 1,3-diene from enyl iodine and organoborate reagent

Scheme 9. Palladium catalyzed synthesis of 1,3-diene from acrylate and enyl bromide

Scheme 10. Palladium catalyzed synthesis of 1,3-diene through olefin sugar alkenyl reaction

Scheme 11. Palladium catalyzed synthesis of 1,3-diene from olefin and organoboride

Scheme 12. Palladium catalyzed synthesis of 1,3-diene by the Heck olefin reaction and the reaction mechanism

Scheme 13. Palladium-catalyzed synthesis of asymmetric 1,3-diene by the C—H activation of olefins

Scheme 14. Palladium catalyzed synthesis of asymmetric 1,3-diene by Heck olefin reaction and its application

Scheme 15. Palladium catalyzed synthesis of 1,3-diene from biphene and organic boron reagents

Scheme 16. Palladium catalyzed synthesis of 1,3-diene from isomerization of binene

Scheme 17. Palladium-catalyzed the synthesis of 1,3-diene by C—H activation of dienes

Scheme 18. Palladium catalyzed synthesis of 1,3-diene from biphene and aryl iodide

Scheme 19. Palladium catalyzed synthesis of 1,3-diene from aryl halogenated hydrocarbons and sulfolene

Scheme 20. Palladium catalyzed synthesis of 1,3-diene from aryl sulfonate and sulfolene

Scheme 21. Palladium catalyzed synthesis of 1,3-diene from aryl electrophiles and cyclobutylene sulfone and its reaction mechanism

Scheme 22. Palladium catalyzed Heck cyclization to synthesize 1,3-diene

Scheme 23. Palladium catalyzed synthesis of 1,3-diene from activated olefin and alkyne and its reaction mechanism

Scheme 24. Palladium catalyzed the synthesis of 1,3-diene with propargyl alcohol and organoborate reagent

Scheme 25. Palladium catalyzed synthesis of 1,3-diene from alkynes and its derivatization

Scheme 26. Palladium catalyzed synthesis of 1,3-diene with pronucleophiles and its reaction mechanism

Scheme 27. Palladium catalyzed synthesis of 1,3-diene from alkene and alkyne

Scheme 28. Palladium catalyzed synthesis of 1,3-diene from enynols and aminals

Scheme 29. Palladium catalyzed synthesis of 1,3-diene from allyl alcohol

Scheme 30. Palladium catalyzed synthesis of 1,3-diene from diazo compounds and allyl halides

Scheme 31. Palladium catalyzed dehydrogenation reaction to synthesize 1,3-diene and its application

Scheme 32. Ruthenium-catalyzed alkyne reduction alkenylation to 1,3-diene, and its reaction mechanism

Scheme 33. Ruthenium catalyzed synthesis of 1,3-diene from active alkenes and alkynes

Scheme 34. Ruthenium catalyzed synthesis of 1,3-diene from allyl phosphate ester and alkyne

Scheme 35. Iridium catalyzed synthesis of 1,3-diene by dehydrooxidation of enyne

Scheme 36. Ruthenium catalyzed Heck reaction of olefins to synthesize 1,3-diene

Scheme 37. Ruthenium catalyzed functionalization of diene to synthesize 1,3-diene

Scheme 38. Rhodium catalyzed functionalization of 1,3-diene

Scheme 39. Rhodium catalyzed olefin C—H bond activation alkenylation reaction to synthesize 1,3-diene and its reaction mechanism

Scheme 40. Ruthenium catalyzed remote isomerization of alkenes to synthesize 1,3-diene

Scheme 41. Rhodium catalyzed synthesis of 1,3-diene from α-diazo-γ,δ-unsaturated esters

Scheme 42. Nickel catalyzed self-coupling of alkenyl electrophile to 1,3-diene

Scheme 43. Nickel catalyzed self-coupling of alkenyl electrophiles into 1,3-diene

Scheme 44. Nickel catalyzed synthesis of 1,3-diene by one-pot reaction of tetrafluoroethylene, alkyne and olefin

Scheme 45. Nickel and palladium cocatalyzed reduction coupling reaction of alkene-based electrophiles to synthesize 1,3-diene

Scheme 46. Nickel catalyzed reduction coupling of alkenyl electrophiles to synthesize 1,3-diene

Scheme 47. Nickel catalyzed synthesis of 1,3-diene by Kumada coupling reaction and its reaction mechanism

Scheme 48. Nickel-photosynergistic catalyzed synthesis of 1,3-diene through alkyne bifunctional groupation reaction and its reaction mechanism

Scheme 49. Synthesis of 1,3-diene involved copper-lithium reagents

Scheme 50. Copper catalyzed synthesis of functionalized 1,3-diene through one-pot reaction of dialkyne, aryl halocarbons and thiols

Scheme 51. Coppe catalyzed synthesis of 1,3-diene from alkynes and enyl sulfonates

Scheme 52. Coppe catalyzed synthesis of 1,3-diene through alkyne functional group reaction

Scheme 53. Copper-catalyzed ring-opening defluoroboronation of difluorocyclobutene to synthesize 1,3-diene

Scheme 54. Copper and palladium co-catalyzed synthesis of 1,3-diene by alkyne bifunctional grouping

Scheme 55. Tin catalyzed radical reaction of bromoallyl hydrazone to synthesize 1,3-diene

Scheme 56. Iron catalyzed synthesis of 1,3-diene through Kumada coupling reaction

Scheme 57. Iron catalyzed synthesis of 1,3-diene from alkenyl iodine and alkenyl lithium

Scheme 58. Praseodymium involving synthesis of 1,3-diene from allyl halogenates and ketones

Scheme 59. Titanium catalyzed intramolecular cyclization of alkynes and ketones to synthesize 1,3-diene

Scheme 60. Cobalt catalyzed hydrogenation cyclization of 1,6-diynylboron to synthesize 1,3-diene

Scheme 61. Cobalt photococatalytic cross-coupling of alkenes to 1,3-diene

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