多组分参与的氟烷基化反应研究进展

doi:10.6023/cjoc202007025

摘要/Abstract

多组分参与的氟烷基化反应是当前有机氟化学研究的一个热点. 在过去的几年里, 由于新试剂新方法的不断涌现, 多组分参与的氟烷基化反应取得了长足的进展, 不仅可以经济有效地一步将氟烷基基团与其他官能团同步引入, 而且可以将起始原料转化为多种含有生物活性或药物活性的化合物. 按照三组分二氟烷基化反应、三组分三氟甲基化反应、三组分全氟烷基化反应、三组分单氟烷基化反应、三组分氟化反应以及四组分氟烷基化反应和总结7个部分, 总结了多组分参与的氟烷基化反应在过去近十年时间里的发展进程, 同时对该类反应进行了总结和展望.

关键词: 多组分, 双官能团化, 二氟烷基化, 三氟甲基化, 全氟烷基化, 单氟烷基化, 氟化反应

Multi-component fluoroalkylation is a hot topic in organic fluorine chemistry. In the past few years, due to the development of new reagents and new methods, multi-component fluoroalkylation reactions have made great progress. It can not only introduce fluoroalkyl groups with other functional groups in one step economically and effectively, but also transform the starting materials into a variety of compounds with biological or pharmaceutical. The development of multi-component fluoroalkylation over the past decade is reviewed from seven parts: three-component difluoroalkylation reaction, three-component trifluoroalkylation reaction, three-component perfluoroalkylation reaction, three-component monofluoro- alkylation reaction, three-component fluorination and four-component fluoroalkylation and conclusion. At the same time, this kind of reaction is summarized and prospected.

Key words: multicomponent, bifunctionalization, difluoroalkylation, trifluoromethylation, perfluoroalkylation, monofluoroalkylation, fluorination

引用此文

潘军, 吴晶晶, 吴范宏. 多组分参与的氟烷基化反应研究进展[J]. 有机化学, 2021, 41(3): 983-1001.

Jun Pan, Jingjing Wu, Fanhong Wu. Progress in Fluoroalkylation of Multicomponent[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 983-1001.

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图/表 68

图式1. 光催化烯烃的羟基二氟甲基化反应

Scheme 1. Hydroxydifluoromethylation of styrenes using photoredox catalysis

图式2. 光催化烯烃的芳基二氟烷基化反应

Scheme 2. Aryldifluoroalkylation of styrenes using photoredox catalysis

图式3. 铁催化烯烃的硫二氟烷基化反应

Scheme 3. Ir(ppy)3/FeCl2 catalyzed suldifluoroalkylation of alkenes

图式4. 光催化未活化烯烃的1,6-双官能团化反应

Scheme 4. 1,6-Difunctionalization of unactivated alkenes using photoredox catalysis

图式5. 光催化烯烃的氰基二氟甲基化

Scheme 5. Photocatalyzed cyanodifluoromethylation of alkenes

图式6. 镍催化烯烃的芳基二氟烷基化反应

Scheme 6. Ni-catalyzed aryldifluoroalkylation of alkenes

图式7. 镍催化烯烃的烷基二氟烷基化反应

Scheme 7. Ni-catalyzed alkyldifluoroalkylation of alkenes

图式8. 镍催化的1,3-烯炔的碳氟烷基化反应

Scheme 8. Ni-catalyzed carbofluoroalkylation of 1,3-enynes

图式9. 铜催化活化烯烃的硫二氟烷基化反应

Scheme 9. Cu-catalyzed suldifluoroalkylation of actived alkenes

图式10. 钴催化烯烃的过氧化二氟烷基化反应

Scheme 10. Co-catalyzed peroxidedifluoroalkylation of alkenes

图式11. 钯催化炔烃的芳基二氟烷基化反应

Scheme 11. Pd-catalyzed aryldifluoroalkylation of alkynes

图式12. 铜催化炔烃的氰基二氟烷基化反应

Scheme 12. Cu-catalyzed cyano-difluoroalkylation of alkynes

图式13. 钯催化炔烃的膦氧二氟烷基化反应

Scheme 13. Pd-catalyzed phosphinodifluoroalkylation of alkynes

图式14. 钯催化炔烃的芳基二氟烷基化反应

Scheme 14. Pd-catalyzed aryldifluoroalkylation of alkynes

图式15. 钯催化炔烃的硼化氟烷基化反应

Scheme 15. Pd-catalyzed fluoroalkylboration of alkynes

图式16. 钯催化炔烃的硼化二氟烷基化反应

Scheme 16. Pd-catalyzed difluoroalkylboration of alkynes

图式17. 含三氟甲基的代表药物

Scheme 17. Drugs containing trifluoromethyl group

图式18. 光催化烯烃的氧三氟甲基化反应

Scheme 18. Oxygentrifluoromethylation of alkenes using photoredox catalysis

图式19. 烯烃的氧三氟甲基化反应

Scheme 19. Oxygentrifluoromethylation of alkenes

图式20. 铜催化烯酰胺的双官能团化反应

Scheme 20. Cu-catalyzed difunctionalization of alkene-amide

图式21. 钌催化烯酰胺的双官能团化反应

Scheme 21. Ru-catalyzed difunctionalization of alkene-amide

图式22. 无金属条件下烯烃的三氟甲基化反应

Scheme 22. Metal-free trifluoromethylation of alkenes

图式23. 铜催化烯酰胺的氧三氟甲基化反应

Scheme 23. Cu-catalyzed oxygentrifluoromethylatio of alkene- amide

图式24. 铜催化烯烃的分子间三氟甲基化反应

Scheme 24. Cu-catalyzed intermolecular trifluoromethylation of alkenes

图式25. 钌催化烯烃的叠氮/胺三氟甲基化反应

Scheme 25. Ru-catalyzed azidotrifluoromethylation and aminotrifluoromethylation of alkenes

图式26. 铜催化烯烃的叠氮三氟甲基化反应

Scheme 26. Cu-catalyzed azidotrifluoromethylation of alkenes

图式27. 铁催化烯烃和N-杂环的叠氮三氟甲基化反应

Scheme 27. Iron-catalyzed azidotrifluoromethylation of olefins and N-heterocycles

图式28. 铜催化烯烃的硫氰基三氟甲基化反应

Scheme 28. Cu-catalyzed trifluoromethylthiocyanation of alkenes

图式29. 光催化末端烯烃的硫三氟甲基化反应

Scheme 29. Sultrifluoromethylation of terminal alkenes using photoredox catalysis

图式30. 铜催化烯烃的氰基三氟甲基化反应

Scheme 30. Cu-catalyzed cyanotrifluoromethylation of alkenes

图式31. 铜催化烯烃的氰基三氟甲基化反应

Scheme 31. Cu-catalyzed cyanotrifluoromethylation of alkenes

图式32. 铜催化烯烃的对映选择性氰基三氟甲基化反应

Scheme 32. Cu-catalyzed enantioselective cyanotrifluoromethylation of alkenes

图式33. 铜催化乙烯基环丙烷的对映选择性1,5-氰基三氟甲基化反应

Scheme 33. Cu-catalyzed enantioselective 1,5-cyanotrifluoro- methylation of vinylcyclopropanes

图式34. 钌催化烯烃的三氟甲基化反应

Scheme 34. Ru-catalyzed Trifluoromethylation of Alkenes

图式35. 铜催化烯烃的氰基氟烷基化反应

Scheme 35. Cu-catalyzed cyanofluoroalkylation of alkenes

图式36. 铜催化1,3-烯炔的三氟甲基氰化反应

Scheme 36. Cu-catalyzed cyanotrifluoromethylation of 1,3- enynes

图式37. 铜催化烯烃的芳基三氟甲基化反应

Scheme 37. Cu-catalyzed aryltrifluoromethylation of alkenes

图式38. 铜催化芳基乙烯的芳基三氟甲基化反应

Scheme 38. Cu-catalyzed aryltrifluoromethylation of aryl-eth- ylene

图式39. 铜催化烯烃与二氧化碳的双官能团化反应

Scheme 39. Cu-catalyzed difunctionalization of alkenes with CO2

图式40. 无金属条件下未活化烯烃的炔基三氟甲基化反应

Scheme 40. Metal-free alkynyltrifluoromethylation of unactived Alkenes

图式41. 铜催化活化烯烃的炔基三氟甲基化反应

Scheme 41. Cu-catalyzed alkynyltrifluoromethylation of actived alkenes

图式42. NHC催化烯烃的酰基三氟甲基化反应

Scheme 42. Acyltrifluoromethylation of alkenes using NHC catalysis

图式43. 铜催化β-三氟甲基化丙烯腈和三氟甲基2H-氮杂丙烯啶的合成

Scheme 43. Cu-catalyzed synthesis of β-trifluoromethylated acrylonitriles and trifluoromethyl-substituted 2H-azirines

图式44. 铜催化活化炔烃的三氟甲基化反应

Scheme 44. Cu-catalyzed trifluoromethylation of alkynes

图式45. 铜催化活化炔烃的氟烷基化反应

Scheme 45. Cu-catalyzed fluoroalkylation of alkynes

图式46. 铜催化芳基硼酸的三氟甲硫基化反应

Scheme 46. Cu-catalyzed sultrifluoromethylation of arylboronic acid

图式47. 无金属条件下未活化烯烃的硼酯全氟烷基化反应

Scheme 47. Metal-free boronperfluoroalkylation of unactived alkenes

图式48. 无金属条件下未活化烯烃的α-全氟烷基-β-杂芳基化反应

Scheme 48. Metal-free α-perfluoroalkyl-β-heteroarylation of unactived alkenes

图式49. 镍催化烯烃的双官能团化反应

Scheme 49. Ni-catalyzed difunctionalization of alkenes

图式50. 铁催化烯烃与炔烃的氮全氟烷基化反应

Scheme 50. Pd-catalyzed nitrogenperfluoroalkylation of alkenes and alkynes

图式51. 铜催化1,3-烯炔的双官能团化反应

Scheme 51. Cu-catalyzed difunctionalization of 1,3-enynes

图式52. 光催化的[3+2+1]成环反应

Scheme 52. [3+2+1]-Annulation using photoredox catalysis

图式53. 光催化硅烯醇醚的全氟烷基化反应

Scheme 53. Perfluoroalkylation of Triisopropylsilane using photoredox catalysis

图式54. 铜催化烯烃的三组分氰基化氟烷基化反应

Scheme 54. Cu-catalyzed three components cyanofluoroalkylation of alkenes

图式55. 铜催化烯烃的三组分叠氮氟烷基化反应

Scheme 55. Cu-catalyzed three components azidofluoroalkylation of alkenes

图式56. 铜催化烯烃的光氧化还原不对称氰基氟烷基化反应

Scheme 56. Cu-catalyzed photoredox asymmetric cyanofluoroalkylation of alkenes

图式57. 钯催化末端炔烃的芳基全氟烷基化反应

Scheme 57. Pd-catalyzed arylperfluoroalkylation of terminal alkynes

图式58. 钯催化炔烃的芳基全氟烷基化反应

Scheme 58. Pd-catalyzed arylperfluoroalkylation of alkynes

图式59. 钯催化炔烃的芳基全氟烷基化反应

Scheme 59. Pd-catalyzed arylperfluoroalkylation of alkynes

图式60. 钯催化炔烃的双官能团化反应

Scheme 60. Pd-catalyzed difunctionalization of alkynes

图式61. 含有氟代三级碳和四级碳的药物分子

Scheme 61. Drug molecules ccontaining fluorinated tertiary and quaternary carbons

图式62. 铜催化烯烃的硼单氟甲基化反应

Scheme 62. Cu-catalyzed boronmonofluoromethylation of alkene

图式63. 银催化未活化烯烃的膦氟化反应

Scheme 63. Silver-catalyzed phosphonofluorination of unactivated alkenes

图式64. 钯催化芳基乙烯的酯基单氟烷基化反应

Scheme 64. Pd-catalyzed estermonofluoroalkylation of aryl- ethylene

图式65. 光催化烯烃的氨基三氟甲基化反应

Scheme 65. Aminotrifluoromethylation of alkenes using photoredox catalysis

图式66. 钴催化烯烃的氟烷基化反应和Kornblum-DeLaMare反应

Scheme 66. Co-catalyzed fluoroalkylation and Kornblum- DeLaMare reaction of styrenes

图式67. 钯催化炔烃的羰基二氟烷基化反应

Scheme 67. Pd-catalyzed carbonyldifluoroalkylation of alkynes

图式68. 钯催化炔烃的羰基二氟烷基化/全氟烷基化反应

Scheme 68. Pd-catalyzed carbonyldifluoroalkylation/carbonyl- perfluoroalkylation of alkynes

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