碘叶立德的化学反应研究进展

doi:10.6023/cjoc202006021

摘要/Abstract

自首个有关叶立德的反应被报道以来, 它们就成为有机化学中的一个重要研究方向. 其中碘叶立德因兼具碘化合物和叶立德的独特反应性受到了人们的广泛关注. 先概括性地阐述了碘叶立德的制备方法和结构性质, 然后对其在有机合成中的应用做了详细的描述, 包括碘叶立德作为有效的卡宾前体在插入反应、环丙烷化反应中的应用及其在环加成反应、重排反应和卤化反应中的研究进展.

关键词: 碘叶立德, 插入反应, 环加成反应, 重排反应, 三氟甲基硫化反应

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

引用此文

仝明慧, 张欣宇, 王也铭, 王自坤. 碘叶立德的化学反应研究进展[J]. 有机化学, 2021, 41(1): 126-143.

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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图/表 50

图式1. 碘叶立德的制备

Scheme 1. Preparation of iodonium ylides

图式2. 烷氧基碘叶立德的合成反应

Scheme 2. Synthesis reaction of alkoxy iodonium ylide

图式3. 羟基碘烷合成邻位取代碘叶立德

Scheme 3. Synthesis ofortho substituted iodonium ylide by hydroxyyiodane

图式4. 金属催化合成碘叶立德

Scheme 4. Metal-catalyzed synthesis of iodonium ylide

图式5. 单羰基碘叶立德的合成反应

Scheme 5. Synthesis of monocarbonyl iodonium ylide

图式6. 极性反转碘叶立德的合成反应

Scheme 6. Synthesis reaction of polarity inversion iodonium ylide

图式7. 环状碘叶立德的合成反应

Scheme 7. Synthesis reaction of cyclic iodonium ylide

图1. 代表性碘叶立德的结构与X射线单晶衍射图

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

图式8. 铑催化的碘叶立德分子内C—H插入反应

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

图式9. 芳基取代的碘苯叶立德分子内C—H插入反应

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

图式10. 碘叶立德与芳香族和噻吩类化合物的插入反应

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

图式11. 碘叶立德与吡咯的插入反应

Scheme 11. Insertion reaction of iodonium ylide with pyrrole

图式12. 碘叶立德与黄酮类化合物的插入反应

Scheme 12. Insertion reaction of iodonium ylide with flavones

图式13. β-酮酰胺分子内C—H插入反应

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

图式14. 碘叶立德与3-取代氧化吲哚衍生物的插入反应

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

图式15. 手性Lewis酸催化β-酮酰胺与碘叶立德的插入反应

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

图式16. 碘叶立德分子内环丙烷化反应

Scheme 16. Intramolecular cyclopropanation of iodonium ylide

图式17. 单羰基碘叶立德合成2-酰基氮杂环丙烷

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

图式18. 碘叶立德合成1,1-环丙烷二酯

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

图式19. 碘叶立德与烯烃的无金属催化环丙烷化反应

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

图式20. 碘叶立德与缺电子烯烃无催化剂环丙烷化反应

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

图式21. Wittig试剂与对碘甲苯原位生成碘叶立德的环丙烷化反应

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

图式22. LED蓝光照射下碘叶立德与烯烃的环丙烷化反应

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

图式23. 环1,3二羰基碘叶立德合成杂环化合物

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

图式24. 环1,3二羰基碘叶立德与PhNCO和PhNCS反应

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

图式25. 碘叶立德与邻硅基三氟甲磺酸酯基芳烃的环加成反应

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

图式26. 碘叶立德与乙炔基酸环化合成2(5H)-呋喃酮

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

图式27. 碘叶立德与亲偶极体的反应制备螺环醇化合物

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

图式28. 碘叶立德与三级胺的环化反应

Scheme 28. Cyclization of iodonium ylide with tertiary amine

图式29. 碘叶立德与对醌甲基化物环化合成2,3-二氢苯并呋喃

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

图式30. 混合膦-碘叶立德与腈类化合物反应

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

图式31. 混合的膦-碘叶立德与乙炔合成取代呋喃和环状膦啉

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

图式32. Doyle-Kirmse反应

Scheme 32. Doyle-Kirmse reactions

图式33. 催化剂控制的选择性[2,3]-和[1,2]-重排反应

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

图式34. 烯丙基碘化物的[1,2]-重排反应

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

图式35. 烯丙基碘化物重排反应机理

Scheme 35. Allyl iodide rearrangement reaction mechanism

图式36. 烯丙基碘化物的[2,3]-重排反应

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

图式37. 碘叶立德与HX试剂的反应

Scheme 37. Reaction of iodonium ylide with HX reagents

图式38. 碘叶立德与PhICl2的反应

Scheme 38. Reaction of iodonium ylide with PhICl2 reagents

图式39. 碘叶立德的放射性氟化反应

Scheme 39. Radiofluorination of iodonium ylide

图式40. 富电子碘叶立德的 18F标记反应

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

图式41. 使用KF/crypt-222配合物的无过渡金属的芳族氟化

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

图式42. 有机化合物的三氟甲基硫化反应

Scheme 42. Trifluoromethylthiolation of organic substrates

图式43. 二氟甲磺酰基碘叶立德与各类化合物的反应

Scheme 43. Reaction of difluoromethanesulfonyl iodonium ylides with various substances

图式44. β-酮酯的不对称亲电二氟甲基硫化反应

Scheme 44. Asymmetric electrophilic difluoromethylthiolation ofβ-keto esters

图式45. 五氟苯磺酰碘叶立德合成全氟苯基硫化合物

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

图式46. 芳基碘叶立德分子间的叶立德转换反应

Scheme 46. Intermolecular transform reaction of aryl iodonium ylide

图式47. 胺与碘叶立德对烯烃的丙二酰化反应

Scheme 47. Malonylamination of alkenes with amines and iodonium ylides

图式48. 碘苯叶立德与路易斯碱之间的单电子转移反应

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

图式49. 碘叶立德的1,3-碳硼化反应

Scheme 49. 1,3-Carboboration of iodonium ylide

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