Research Progress of Vinyl/Aryl Phosphonium Salts in Organic Synthesis

doi:10.6023/cjoc202107065

Abstract

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

Cite this article

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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Fig. & Tab. 43

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

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

Scheme 2. Reduction of alkyne derivatives to alkene derivatives

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

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

Scheme 5. Proposed mechanism of cis-trans isomerization

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

Scheme 7. Two proposed mechanisms

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

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

Scheme 10. Z-Selective reduction of alkyne derivatives

Scheme 11. Products from certain Stille reaction

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

Scheme 13. Palladium catalyzed carbonylation of aryl-phosphonium salts

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

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

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

Scheme 17. Cobalt catalyzed alkylation with heteroaryl-phosphonium salts

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

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

Scheme 20. Different reactivities of carbanion positions

Scheme 21. Nucleophilic arylation with aryl-phosphonium salts

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

Scheme 23. Arynes involved aryl nucleophilic reactions

Scheme 24. Site-selective incorporation of deuterium

Scheme 25. 2-Position-selective functionalization

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

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

Scheme 28. Ligand coupling reaction based on phosphine oxide

Scheme 29. Ligand coupling of heteroaryl-phosphonium salts

Scheme 30. Ligand coupling of biheteroaryl-phosphonium salts

Scheme 31. Biheteroaryls via ligand coupling

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

Scheme 33. Proposed mechanism for the radical pathway to dipyridyls

Scheme 34. Preparation of heteroaryl-phosphonium salts

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

Scheme 36. Reaction of bisphosphonium salt with nucleophiles

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

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

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

Scheme 40. Introduction of aromatic heteronucleophiles

Scheme 41. Reaction with thiazole-phosphonium salts

Scheme 42. Selective halogenation of heteroaryl-phosphonium salts

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