乙烯基/芳基鏻盐在有机合成中的研究进展

doi:10.6023/cjoc202107065

摘要/Abstract

膦类化合物由于在有机合成反应中作为高效配体、催化剂以及化学计量还原剂等一直受到研究者们的广泛关注, 然而鏻盐作为有机膦类化合物的一类重要衍生物, 在有机合成中的应用主要集中在Wittig反应、Staudinger反应或者作为反应中间体. 在过去很长一段时间里, 乙烯基/芳基鏻盐的反应仅有零星的报道. 近几年, 随着新方法的不断涌现, 乙烯基/芳基等不同官能团的引入使得乙烯基/芳基鏻盐的应用取得了快速的进展, 也为具有生物活性或药物活性的化合物的合成提供了新思路. 根据鏻盐的种类和反应的类型综述了近几年来通过乙烯基/芳基鏻盐构建/引入乙烯基和芳基官能团的有机合成反应的研究进展.

关键词: 乙烯基鏻盐, 芳基鏻盐, 有机合成

Phosphines have attracted much attention as efficient ligands, catalysts or stoichiometric reductants in organic synthesis. However, the application of phosphonium salts, as a kind of important derivatives of phosphines, has focused on Wittig reaction, Staudinger reaction or other reactions as intermediates. With the rapid development of new methods, the introdcution of vinyl/aryl groups not only makes a considerable progress in the applications of vinyl/aryl phosphonium salts, but provides novel strategies for the synthesis of bioactive or pharmaceutical molecules. The review is summarized based on the types of phosphonium salts and reactions to construct vinyl/aryl groups in recent years.

Key words: vinyl phosphonium salt, aryl phosphonium salt, organic synthesis

引用此文

黄卫春, 丁欣宇, 訾由. 乙烯基/芳基鏻盐在有机合成中的研究进展[J]. 有机化学, 2022, 42(2): 471-486.

Weichun Huang, Xinyu Ding, You Zi. Research Progress of Vinyl/Aryl Phosphonium Salts in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 471-486.

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图/表 43

图式1. 乙烯基鏻盐合成环己烯类衍生物

Scheme 1. Synthesis of cyclohexene derivates from vinyl- phosphonium salt

图1. 原位生成的Wittig试剂与醛的缩合产物

Figure 1. Condensation products of in situ formed Wittig reagents with aldehydes

图式2. 炔类化合物还原为烯类化合物

Scheme 2. Reduction of alkyne derivatives to alkene derivatives

图式3. 由活化炔基合成1,2-二氘代烯烃

Scheme 3. Synthesis of 1,2-dideuteriated olefins from activated acetylenes

图式4. 选择性合成α-和β-氘代烯类化合物

Scheme 4. Selective synthesis of α- and β-deuteriated alkene derivatives

图式5. cis-trans异构化的可能机理

Scheme 5. Proposed mechanism of cis-trans isomerization

图式6. PPh3促进炔基酮合成E构型查尔酮

Scheme 6. E-Chalcones from ynones in the presence of PPh3

图式7. 两种可能的机理

Scheme 7. Two proposed mechanisms

图式8. 乙烯基鏻盐制备吡啶基乙烯基膦氧

Scheme 8. Pyridyl-vinyl-phosphine oxides from vinyl-phospho- nium salts

图式9. 炔类化合物还原至E和Z构型烯类化合物

Scheme 9. Reduction of alkyne derivatives to both E- and Z- alkene derivatives

图式10. 炔类化合物的Z-选择性还原

Scheme 10. Z-Selective reduction of alkyne derivatives

图式11. Stille反应产物

Scheme 11. Products from certain Stille reaction

图12. 芳基鏻盐在Stille反应中的作用

Scheme 12. Role of aryl-phosphonium salt in Stille reaction

图式13. 钯催化芳基鏻盐的酰化反应

Scheme 13. Palladium catalyzed carbonylation of aryl-phosphonium salts

图式14. 芳基鏻盐参与的Heck反应中的阴离子效应

Scheme 14. Anionic effects on Heck reaction with aryl-phosphonium salts

图式15. 芳基鏻盐参与的Heck、Suzuki以及Sonogashira反应

Scheme 15. Heck, Suzuki as well as Sonogashira reactions with aryl-phosphonium salts

图式16. Ni催化的杂芳基鏻盐的偶联反应

Scheme 16. Nickel catalyzed coupling reaction with heteroaryl-phosphonium salts

图式17. Co催化的杂芳基鏻盐的烷基化反应

Scheme 17. Cobalt catalyzed alkylation with heteroaryl-phosphonium salts

图式18. Pd催化的杂芳基鏻盐的偶联反应

Scheme 18. Pd-catalyzed coupling reactions with heteroaryl-phosphonium salts

图式19. 吡啶三苯基鏻盐作为芳基亲核试剂前体

Scheme 19. Pyridyl-triphenyl-phosphonium salt as aryl nucleophile precursor

图式20. 不同的活性位点

Scheme 20. Different reactivities of carbanion positions

图式21. 芳基鏻盐的亲核芳基化反应

Scheme 21. Nucleophilic arylation with aryl-phosphonium salts

图式22. 芳基鏻盐参与芳基化反应的可能机理

Scheme 22. Proposed mechanism for the arylation with aryl- phosphonium salts

图23. 苯炔参与的芳基亲核反应

Scheme 23. Arynes involved aryl nucleophilic reactions

图式24. 位点选择性氘代

Scheme 24. Site-selective incorporation of deuterium

图式25. 2位选择性官能团化

Scheme 25. 2-Position-selective functionalization

图式26. 烷基三苯基鏻盐作为亲核芳基化前体的应用

Scheme 26. Application of alkyl-triphenyl-phosphonium salts as nucleophilic arylation precursors

图式27. 配体偶联反应得到二甲基二碘化物

Scheme 27. Dimethiodide of 2,2'-bipyrid from ligand coupling

图式28. 基于膦氧的配体偶联反应

Scheme 28. Ligand coupling reaction based on phosphine oxide

图式29. 杂芳基鏻盐的配体偶联反应

Scheme 29. Ligand coupling of heteroaryl-phosphonium salts

图式30. 二杂芳基鏻盐的配体偶联反应

Scheme 30. Ligand coupling of biheteroaryl-phosphonium salts

图式31. 配体偶联构建联芳环化合物

Scheme 31. Biheteroaryls via ligand coupling

图式32. 与金属催化偶联反应的对比

Scheme 32. Comparison to metal-catalyzed cross-coupling reactions

图式33. 自由基合成联吡啶的可能机理

Scheme 33. Proposed mechanism for the radical pathway to dipyridyls

图式34. 制备杂芳基鏻盐

Scheme 34. Preparation of heteroaryl-phosphonium salts

图式35. 吡啶鏻盐的初步研究

Scheme 35. Preliminary investigation of pyridyl-triphenyl- phosphonium salt

图式36. 双鏻盐与亲核试剂的反应

Scheme 36. Reaction of bisphosphonium salt with nucleophiles

图式38. 由杂芳基鏻盐选择性合成杂芳基硫醚和杂芳胺

Scheme 38. Selective thiolation and amination from heteroaryl-phosphonium salts

图式37. 由杂芳基鏻盐选择性合成杂芳基醚

Scheme 37. Selective formation of heteroaryl ethers from heteroaryl-phosphonium salts

图式39. 杂芳基鏻盐的亲核加成机理

Scheme 39. Mechanism for the nucleophilic addition of heteroaryl-phosphonium salts

图式40. 芳基杂原子亲核试剂的反应

Scheme 40. Introduction of aromatic heteronucleophiles

图式41. 噻唑鏻盐参与的反应

Scheme 41. Reaction with thiazole-phosphonium salts

图式42. 杂芳基鏻盐的选择性卤代反应

Scheme 42. Selective halogenation of heteroaryl-phosphonium salts

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