过渡金属催化烯烃和炔烃合成1,3-共轭二烯化合物研究进展

doi:10.6023/cjoc202210017

摘要/Abstract

1,3-共轭二烯是许多天然产物和药物的关键结构单元. 由于共轭烯烃具有特殊的化学性质, 它们在有机合成和材料科学中起着核心作用. 目前, 1,3-共轭二烯的合成主要是通过过渡金属催化的方法实现, 通过该方法科研工作者构建了一系列1,3-二烯骨架, 丰富了共轭二烯类化合物的结构多样性, 同时也扩展了二烯化合物的应用范围. 以过渡金属催化剂的种类不同为主线, 分类对1,3-二烯的合成进行了综述, 并对其发展前景予以展望.

关键词: 过渡金属催化, 1,3-共轭二烯, 有机合成, 应用

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

引用此文

徐光利, 许静, 徐海东, 崔香, 舒兴中. 过渡金属催化烯烃和炔烃合成1,3-共轭二烯化合物研究进展[J]. 有机化学, 2023, 43(6): 1899-1933.

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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图/表 62

图1. 共轭烯烃和多烯天然产物

Figure 1. Conjugated alkenes and polyene natural products

图式1. 钯催化烯基磺酸酯与烯酮合成1,3-二烯

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

图式2. 钯催化烯基磺酸酯与炔烃合成1,3-二烯

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

图式3. 钯催化烯基磺酸酯与烯烃合成1,3-二烯

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

图式4. 钯催化烯基磺酸酯与烯烃合成1,3-二烯

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

图式5. 钯催化肉桂酸与烯基溴代物合成1,3-二烯

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

图式6. 钯催化烯基卤代烃与有机锂试剂合成1,3-二烯

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

图式7. 钯催化烯基溴代物与N-甲苯磺酰腙合成1,3-二烯

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

图式8. 钯催化烯基碘与有机硼试剂合成1,3-二烯

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

图式9. 钯催化丙烯酸酯与烯基溴代物合成1,3-二烯

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

图式10. 钯催化糖烯烯基化反应合成1,3-二烯

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

图式11. 钯催化烯烃与有机硼试剂合成1,3-二烯

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

图式12. 钯催化烯烃Heck反应合成1,3-二烯及反应机理

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

图式13. 钯催化烯烃C—H活化烯基化反应合成不对称1,3-二烯

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

图式14. 钯催化烯烃Heck反应合成不对称1,3-二烯及其应用

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

图式15. 钯催化联烯与有机硼试剂合成1,3-二烯

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

图式16. 钯催化联烯异构化合成1,3-二烯

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

图式17. 钯催化联烯C—H活化烯基化反应合成1,3-二烯

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

图式18. 钯催化联烯与芳基碘代物合成1,3-二烯

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

图式19. 钯催化芳基卤代烃与环丁烯砜合成1,3-二烯

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

图式20. 钯催化芳基磺酸酯与环丁烯砜合成1,3-二烯

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

图式21. 钯催化芳基亲电试剂与环丁烯砜合成1,3-二烯及其反应机理

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

图式22. 钯催化Heck环化反应合成1,3-二烯

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

图式23. 钯催化活性烯烃与炔烃合成1,3-二烯及反应机理

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

图式24. 钯催化炔丙醇与有机硼试剂合成1,3-二烯

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

图式25. 钯催化炔烃合成1,3-二烯及其衍生化反应

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

图式26. 钯催化烯炔与亲核试剂合成1,3-二烯及反应机理

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

图式27. 钯催化烯炔与烯烃合成1,3-二烯

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

图式28. 钯催化烯炔醇与胺合成1,3-二烯

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

图式29. 钯催化烯丙醇合成1,3-二烯

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

图式30. 钯催化重氮化合物与烯丙基卤代物合成1,3-二烯

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

图式31. 钯催化脱氢反应合成1,3-二烯及应用

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

图式32. 钌催化炔烃还原烯基化反应合成1,3-二烯其反应机理

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

图式33. 钌催化活性烯烃与炔烃合成1,3-二烯

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

图式34. 钌催化烯丙基磷酸酯与炔烃合成1,3-二烯

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

图式35. 铱催化烯炔去氢氧化反应合成1,3-二烯

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

图式36. 钌催化烯烃间Heck反应合成1,3-二烯

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

图式37. 钌催化二烯功能化反应合成1,3-二烯

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

图式38. 铑催化1,3-二烯功能化反应

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

图式39. 铑催化烯烃C—H键活化烯基化反应合成1,3-二烯及反应机理

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

图式40. 钌催化烯烃远程异构化合成1,3-二烯

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

图式41. 铑催化α-重氮-γ,δ-不饱和酯合成1,3-二烯

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

图式42. 镍催化烯基亲电试剂自偶联合成1,3-二烯

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

图式43. 镍催化烯基亲电试剂自偶联合成1,3-二烯

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

图式44. 镍催化四氟乙烯、炔烃、烯烃一锅法反应合成1,3-二烯

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

图式45. 镍、钯共催化烯基亲电试剂还原偶联反应合成1,3-二烯

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

图式46. 镍催化烯基亲电试剂还原偶联反应合成1,3-二烯

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

图式47. 镍催化Kumada偶联反应合成1,3-二烯及其反应机理

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

图式48. 镍光协同催化炔烃双官能团化反应合成1,3-二烯及反应机理

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

图式49. 铜锂试剂参与的1,3-二烯的合成

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

图式50. 铜催化二炔、芳基卤代烃及硫醇一锅法反应合成功能化1,3-二烯

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

图式51. 铜催化炔烃与烯基磺酸酯合成1,3-二烯

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

图式52. 铜催化炔烃官能团化反应合成1,3-二烯

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

图式53. 铜催化二氟环丁烯开环去氟硼化反应合成1,3-二烯

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

图式54. 铜、钯共催化炔烃双官能团化反应合成1,3-二烯

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

图式55. 锡催化溴代烯丙基腙自由基反应合成1,3-二烯

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

图式56. 铁催化Kumada偶联反应合成1,3-二烯

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

图式57. 铁催化烯基碘与烯基锂试剂合成1,3-二烯

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

图式58. 镨参与的与烯丙基卤代物与酮合成1,3-二烯

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

图式59. 钛催化炔烃与酮分子内环化反应合成1,3-二烯

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

图式60. 钴催化1,6-二炔硼氢化环化反应合成1,3-二烯

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

图式61. 钴、光协同催化烯烃交叉偶联合成1,3-二烯

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

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