可见光介导的三氟甲基的选择性C－F键断裂及其在偕二氟类化合物合成中的应用

doi:10.6023/cjoc202307004

摘要/Abstract

偕二氟类化合物独特的性质使其在医药、材料领域受到广泛关注. 将廉价、易得的三氟甲基转化为偕二氟基团, 在有机合成中具有重要意义, 但是选择性断裂C—F键面临巨大的挑战, 因为三氟甲基中C—F键断裂的解离能远高于产物偕二氟基团中C—F键解离能, 即难以控制C—F键的选择性断裂, 极易发生过度脱氟. 相对于传统热反应, 在可见光促进下, 利用光催化剂敏化底物, 创造一条经过激发态的新反应途径, 可以更加高效、高选择性地实现C—F断裂. 对近三年来利用可见光催化三氟甲基的选择性C－F键断裂制备偕二氟类化合物的研究进展进行了分析和总结, 并对其前景进行了展望.

关键词: 光催化, 自由基, C—F键断裂, 偕二氟化合物, 合成

The unique properties of difluorinated compounds have attracted widespread attention in the fields of medicine and material sciences. The conversion of inexpensive and easily available trifluoromethyl groups into difluoro groups is of great importance in organic synthesis. However, there still exist great challenges in the selective cleavage of C—F bonds, because the dissociation energy of single C—F bond in trifluoromethyl group is much higher than that of the C—F bond in the difluoro unit of the generated product. Thus, the selective cleavage of C—F bond is difficult to control, which can easily lead to excessive defluorination. Compared with the traditional thermal reaction, the visible-light irradiated reaction provides an alternative pathway to achieve C—F cleavage more efficiently and selectively. The research progress on the selective cleavage of C—F bonds mediated by visible light in the past three years is summarized and its future perspective is prospected.

Key words: photocatalysis, free radical, C—F fracture, germinal difluoro-compound, synthesis

引用此文

金玉坤, 任保轶, 梁福顺. 可见光介导的三氟甲基的选择性C－F键断裂及其在偕二氟类化合物合成中的应用[J]. 有机化学, 2024, 44(1): 85-110.

Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.

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图/表 57

图1. 含偕二氟结构的药物和液晶分子

Figure 1. Drugs and liquid crystal molecules containing difluoride structures

图式1. 光催化条件下三种含有三氟甲基底物的C—F键断裂

Scheme 1. C—F bond cleavage in three types of substrates containing trifluoroalkyl groups under photocatalytic conditions

图式2. 光催化三氟甲基芳烃的脱氟氢化

Scheme 2. Organophotoredox hydrodefluorination of trifluoromethylarenes

图式3. 可见光催化C—F键断裂与CO2的选择性羧基化反应

Scheme 3. Visible-light photoredox-catalyzed selective carboxylation of C—F bonds with CO2

图式4. 可见光诱导对氰基三氟甲苯与苯乙烯的自由基-极性交叉偶联

Scheme 4. Radical-polar cross-coupling between p-cyanotri- fluorotoluene and arylene promoted by visible light

图式5. 芳基硫醇盐作为双功能催化剂的脱氟烷基化反应

Scheme 5. Aromatic thiols as bifunctional catalysts for photocatalytic defluorination and alkylation

图式6. 可见光催化三氟甲基芳烃与腙的脱氟烷基化反应

Scheme 6. Visible-light catalyzed defluoroalkylation of trifluoromethyl aromatic hydrocarbons with hydrazone

图式7. 可见光介导三氟甲基芳烃脱氟硫醚化反应

Scheme 7. Visible light-mediated defluorination and thioetherification of trifluoromethyl aromatic hydrocarbons

图式8. 光催化三氟甲基芳烃与未活化烯烃的可控脱氟烷基化及远端羰基化反应

Scheme 8. Photocatalytic controllable defluoroalkylation and distal carbonylation of trifluoromethyl aromatics with unactivated olefins

图式9. 可见光诱导钯催化三氟甲基芳烃与硼酸的选择性脱氟芳基化反应

Scheme 9. Visible-light-induced Pd-catalyzed selective defluoroarylation of trifluoromethylarenes with arylboronic acid

图式10. 稀土光催化剂介导的脱氟氢化反应

Scheme 10. Rare earth photocatalyst-mediated defluoroalkylation

图式11. 可见光介导α-三氟甲基烯烃的脱氟/缩醛化反应

Scheme 11. Visible light-mediated defluorination/acetalation of α-trifluoromethyl olefins

图式12. 光氧化还原有机锌试剂活化卤代烷与α-三氟甲基苯乙烯的Barbier型反应

Scheme 12. Barbier-type reaction of halogenated alkanes with α-trifluoromethyl styrene activated by photoredox organozinc reagent

图式13. 可见光介导酰胺中未活化C?H键的远程区域选择性官能化反应

Scheme 13. Visible light-mediated remote region-selective functionalization of unactivated C?H bonds in amides

图式14. 可见光诱导一锅合成法合成CF2取代环丁烯衍生物

Scheme 14. Synthesis of CF2-substituted cyclobutene derivatives by visible light-induced one-pot synthesis

图式15. 可见光介导的β,γ-不饱和腙与α-三氟甲基烯烃的连续自由基环化脱氟反应

Scheme 15. Visible light-mediated continuous radical cyclization defluorination of β,γ-unsaturated hydrazone with α-trifluoro- methyl olefins

图式16. 光催化α-三氟甲基烯烃与烷基碘化物通过C—F键断裂构建偕二氟烯烃衍生物

Scheme 16. Construction of difluoroolefin derivatives by photocatalysis of α-trifluoromethyl olefin and alkyl iodide by C—F bond cleavage

图式17. 可见光催化的硅烷二氟烯丙基化反应

Scheme 17. Visible light-catalyzed difluoroallylation of silane

图式18. 可见光介导三氟甲基烯烃和烷基硅烷脱氟硅烷化反应

Scheme 18. Defluorosilanization of trifluoromethyl olefins and alkyl silanes mediated by visible light

图式19. 可见光氧化还原催化α-三氟甲基烯烃脱氟芳氧甲基化

Scheme 19. Visible light-mediated photoredox catalyzed defluo- rination of α-trifluoromethyl olefins

图式20. 可见光催化α-三氟甲基烯烃与叔胺二氟烯丙基化反应

Scheme 20. Photocatalytic difluoroallylation of α-trifluoro- methyl olefins with tertiary amines

图式21. 光诱导环烷氧基对氟化烯烃开环加成合成远端氟烯基酮

Scheme 21. Visible light-induced cycloaddition of cycloalkoxy to fluorinated olefins to synthesize distal fluoroalkenyl ketones

图式22. 可见光催化通过双C-F键裂解合成5-氟二氢吲哚嗪类衍生物

Scheme 22. Synthesis of 5-fluorodihydroindolazine derivatives by double C-F bond cleavage catalyzed by visible light

图式23. 以BTP作为偶联剂的N-芳基氨基酸的光催化脱氟反应

Scheme 23. Photocatalytic defluorination of N-aryl amino acids using BTP as coupling agent

图式24. 光氧化还原催化的草酸酯的偕二氟烯丙基化反应

Scheme 24. Photoredox-catalyzed allylation of oxalate with difluoroallylation

图式25. 未活化烯烃的三组分三氟甲基化二氟烯丙基化反应

Scheme 25. Three-component trifluoromethylation difluoroallylation of unactivated olefins

图式26. 可见光催化一锅两步法合成单氟环戊烯

Scheme 26. One-pot two-step synthesis of monofluorocyclopentene catalyzed by visible light

图式27. 可见光诱导脱羧/脱氟硅烷化合成偕二氟烯

Scheme 27. Visible light-induced decarboxylation/defluorosila- nization to synthesize carboxylenes

图式28. 可见光催化α-三氟甲基烯烃与空间位阻伯胺反应合成偕二氟烯丙基芳烃

Scheme 28. Synthesis of cardifluoroallyl aromatics catalyzed by visible light reaction of α-trifluoromethyl olefins with spatially impeded primary amines

图式29. 多重催化协同作下的烷基醛和环酮β-位碳氢的直接偕二氟烯丙基化反应

Scheme 29. Direct difluoroallylation of alkyl aldehyde and cycloketone β-hydrocarbons under synergistic action of multiple

图式30. 多重催化协同作下的烷基醛和环酮β-位碳氢的直接偕二氟烯丙基化反应

Scheme 30. Direct difluoroallylation of alkyl aldehyde and cycloketone β-hydrocarbons under synergistic action of multiple catalysts

图式31. 光氧化还原/Lewis碱双重催化下烷基硼酸与三氟甲基苯乙烯的脱氟烷基化反应

Scheme 31. Defluorination and alkylation of alkyl boric acid with trifluoromethyl styrene under photoredox/Lewis base double catalysis

图式32. 以N-杂环卡宾(NHC)-BH3配合物作为硼基前体实现脱氟硼化反应

Scheme 32. Defluorination and boronation using N-heterocyclic carbene (NHC)-BH3 complex as boron-based precursor

图式33. 可见光催化α-三氟甲基芳烯烃与伯、仲和叔烷基碘的官能化

Scheme 33. See photocatalytic functionalization of α-trifluoro- methyl aromatic olefins with primary, secondary and tertiary alkyl iodides

图式34. Mn2(CO)10和铱基光催化剂结合催化下的烷基碘的偕二氟烯丙基化反应

Scheme 34. Difluoroallylation of alkyl iodine catalyzed by the combination of Mn2(CO)10 and iridium-based photocatalysts

图式35. 光氧化还原/氢原子转移共催化酰胺、醚和烷基醛的C—H二氟烯丙基化反应

Scheme 35. Photoredox/hydrogen atom transfer co-catalysis of C—H difluoroallylation of amide, ether and alkyl aldehyde

图式36. 二级酰胺的位点选择性脱氟C(sp3)—H烷基化反应

Scheme 36. Selective defluorination of C(sp3)—H alkylation by check point of secondary amides

图式37. 光氧化还原/Br?nsted碱协同催化的氨基二氟烯丙基化反应

Scheme 37. Photoredox/Br?nsted base synergistic catalysis of amino-difluoroallylation

图式38. 基于糖基自由基的光催化脱氟偕二氟烯丙基化反应合成碳烷基糖苷

Scheme 38. Synthesis of carboalkyl glycosides by photocatalytic defluorination and difluoroallylation based on glycosyl radicals

图式39. 还原猝灭引发、催化剂控制的α-CF3烯烃的发散性烷基化

Scheme 39. Catalyst-controlled divergent alkylation of α-CF3 olefins initiated by reduction quenching

图式40. 基于环烷醇光催化脱氟开环偕二氟烯丙基化反应

Scheme 40. Ring-opening and difluoroallylation based on photocatalytic defluorination of naphthenic alcohols

图式41. 可见光催化环丙醇与α-三氟甲基取代烯烃的串联反应

Scheme 41. Visible light catalyzed series reaction of cyclopropanol with α-trifluoromethyl substituted olefins

图式42. 可见光介导的三氟甲基烯烃与醇草酸酯衍生物脱氟烷氧羰基化反应

Scheme 42. Visible light-mediated defluoroalkoxycarbonylation of trifluoromethyl olefins with alcohol oxalate derivatives

图式43. 光氧化还原催化自由基加成/脱氟烷基化偶联反应

Scheme 43. Photoredox catalyzed free radical addition/defluo- roalkylation coupling reaction

图式44. 芳基磺盐参与的光化学后期脱氟反应

Scheme 44. Photochemical defluorination reaction involved by aryl sulfonate

图式45. 可见光催化碘代烷与α-三氟甲基苯乙烯的脱氟羰基化偶联

Scheme 45. Visible light-catalyzed defluorination and carbonylation coupling reaction of iodized alkanes with α-trifluoromethyl styrene

图式46. 可见光促进自由基[1,2]-Brook重排反应

Scheme 46. Visible light promotes free radical [1,2]-Brook rearrangement reaction

图式47. 光/镍双催化脱氟磺酰化合成偕二氟烯丙基砜的反应

Scheme 47. Synthesis of difluoroallyl sulfone by photocatalytic/nickel double-catalytic defluorosulfonylation

图式48. 光催化二芳基酮介导的多氟乙酰胺和三氟乙酸酯的脱氟官能化反应

Scheme 48. Photocatalytic defluorination functionalization of polyfluoroacetamide and trifluoroacetate mediated by diarylketone

图2. 光催化二芳基酮介导的多氟乙酰胺和三氟乙酸酯药物分子的后修饰

Figure 2. Photocatalytic diarylketone-mediated post-modifi- cation of polyfluoroacetamide and trifluoroacetate drug molecules

图式49. 可见光氧化还原催化多氟脂肪族酰胺和酯的脱氟功能化

Scheme 49. Defluorination functionalization of polyfluorinated aliphatic amids and esters catalyzed by visible light redox

图式50. 邻膦酚光催化三氟甲基脱氟烷基化和脱氟加氢反应

Scheme 50. Photocatalytic defluoroalkylation and hydrode- fluorination of trifluoromethyls using o-phosphinophenolate

图式51. 光催化芳基二硫化物介导的三氟甲基C-F键活化

Scheme 51. Photocatalytic aryl disulfide-mediated trifluoromethyl C-F bond activation

图式52. 可见光催化硫酚介导的偕二氟氧化吲哚骨架的构建

Scheme 52. Visible light-catalyzed thiophenol-mediated construction of indole skeleton with difluoroxide

图式53. 可见光氧化还原催化HFIP辅助三氟甲基酮的单C-F键活化

Scheme 53. HFIP assisted single C-F bond activation of trifluoromethyl ketones using visible-light photoredox catalysis

图式54. 可见光氧化还原催化溶剂控制的三氟甲基酮单C—F键活化

Scheme 54. Single C—F bond activation of trifluoromethyl ketone controlled by visible light redox catalytic solvent

图式55. 可见光诱导硫醇催化下三氟甲基苯并咪唑脱氟烷基化反应

Scheme 55. Visible light induced direct C(sp3)-F alkylation of trifluoromethyl benzimidazole catalyzed by thiol

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