Advances in Reactions of Iodonium Ylides

doi:10.6023/cjoc202006021

Abstract

Since the first reaction involved ylides was reported, they have been an important research direction of organic chemistry. Among them, iodonium ylides attracted considerable attentions in organic synthesis due to their unique reactivities as both iodine source and ylides. The preparation methods and structural properties of iodonium ylides are generally elaborated. Then, the reactivities of iodonium ylides are reviewed in detal, including the application of iodonium ylides as a carbene precursor in insertion reactions, cyclopropane reactions, and their development research in cycloaddition reactions, rearrangement reactions and halogenation reaction.

Key words: iodonium ylide, insertion reaction, cycloaddition reaction, rearrangement reaction, trifluoromethylthiolation

Cite this article

Minghui Tong, Xinyu Zhang, Yeming Wang, Zikun Wang. Advances in Reactions of Iodonium Ylides[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 126-143.

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Fig. & Tab. 50

Scheme 1. Preparation of iodonium ylides

Scheme 2. Synthesis reaction of alkoxy iodonium ylide

Scheme 3. Synthesis ofortho substituted iodonium ylide by hydroxyyiodane

Scheme 4. Metal-catalyzed synthesis of iodonium ylide

Scheme 5. Synthesis of monocarbonyl iodonium ylide

Scheme 6. Synthesis reaction of polarity inversion iodonium ylide

Scheme 7. Synthesis reaction of cyclic iodonium ylide

Figure 1. Structures and X-ray single crystal diffraction patterns of representative iodonium ylids

Scheme 8. Rhodium-catalyzed intramolecular C—H insertion reaction of iodonium ylide

Scheme 9. Intramolecular C—H insertion reaction of aryl substituted iodonium ylide

Scheme 10. Insertion reaction of iodonium ylide with aromatic compounds and thiophene

Scheme 11. Insertion reaction of iodonium ylide with pyrrole

Scheme 12. Insertion reaction of iodonium ylide with flavones

Scheme 13. Intramolecular C—H insertion reaction ofβ-keto- amide

Scheme 14. Insertion reaction of iodonium ylide with 3-substi- tuted oxindoles

Scheme 15. Insertion reaction of iodonium ylide withβ-keto- amides catalyzed by chiral Lewis acid

Scheme 16. Intramolecular cyclopropanation of iodonium ylide

Scheme 17. Synthesis of 2-acyl aziridine from monocarbonyl iodonium ylide

Scheme 18. Synthesis of 1,1-cyclopropane diester by iodonium ylide

Scheme 19. Metal-free catalytic cyclopropanation of iodonium ylide and olefins

Scheme 20. Catalyst-free cyclopropanation of iodonium ylide and electron-deficient olefins

Scheme 21. Cyclopropanation of iodonium ylide generated in situ from Wittig reagent andp-iodotoluene

Scheme 22. Cyclopropane reaction of olefin and iodonium ylide under blue LED irradiation

Scheme 23. Synthesis of heterocyclic compounds with cyclic 1,3-dicarbonyl iodonium ylide

Scheme 24. Reaction of cyclic 1,3-dicarbonyl iodonium ylide with PhNCO and PhNCS

Scheme 25. Cycloaddition reaction of iodonium ylide withortho-silyl aryltriflates

Scheme 26. Synthesis of 2(5H)-furanone by cyclization of iodo- nium ylide with acetylenic acids

Scheme 27. Preparation of spirocyclic alcohol by the reaction of iodonium ylide and dipolephile

Scheme 28. Cyclization of iodonium ylide with tertiary amine

Scheme 29. Synthesis of 2,3-dihydrobenzofuran by cyclization of iodonium ylide withpara-quinone methides

Scheme 30. Reaction of mixed phosphine-iodonium ylide with nitrile compounds

Scheme 31. Synthesis of substituted furans and annelated phosphinolines from mixed phosphine- iodonium ylide and acetylene

Scheme 32. Doyle-Kirmse reactions

Scheme 33. Catalyst-controlled selective [2,3]- and [1,2]-rear- rangement reactions

Scheme 34. [1,2]-Rearrangement reaction of allyl iodide

Scheme 35. Allyl iodide rearrangement reaction mechanism

Scheme 36. Scheme 36 [2,3]-rearrangement reaction of allyl iodide

Scheme 37. Reaction of iodonium ylide with HX reagents

Scheme 38. Reaction of iodonium ylide with PhICl2 reagents

Scheme 39. Radiofluorination of iodonium ylide

Scheme 40. Scheme 40 18F labeling reaction of electron rich iodonium ylide

Scheme 41. Transition metal free, aromatic fluorination using a KF/crypt-222 complex

Scheme 42. Trifluoromethylthiolation of organic substrates

Scheme 43. Reaction of difluoromethanesulfonyl iodonium ylides with various substances

Scheme 44. Asymmetric electrophilic difluoromethylthiolation ofβ-keto esters

Scheme 45. Synthesis of sulfur perfluorophenyl compounds using a pentafluorobenzenesulfonyl iodonium ylide

Scheme 46. Intermolecular transform reaction of aryl iodonium ylide

Scheme 47. Malonylamination of alkenes with amines and iodonium ylides

Scheme 48. Single electron transfer reaction between iodonium ylide and Lewis base

Scheme 49. 1,3-Carboboration of iodonium ylide

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