电化学促进的烯烃和炔烃双官能团化反应研究进展

doi:10.6023/cjoc202204066

有机化学 ›› 2022, Vol. 42 ›› Issue (12): 4169-4201.DOI: 10.6023/cjoc202204066 上一篇下一篇

所属专题：自由基化学专辑

综述与进展

电化学促进的烯烃和炔烃双官能团化反应研究进展

李秀英, 陶萍芳, 程泳渝, 胡琼, 黄伟娟, 李芸, 罗志辉^*(), 黄国保^*()

玉林师范学院广西农产资源化学与生物技术重点实验室广西玉林 537000

收稿日期:2022-04-27 修回日期:2022-06-13 发布日期:2022-09-08
通讯作者: 罗志辉, 黄国保
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(21961042); 广西高校中青年教师基础能力提升(2021KY0587); 广西高校中青年教师基础能力提升(2022KY0572); 玉林师范学院科研(G2021ZK16); 玉林师范学院科研(G2022ZK08)

Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes

Xiuying Li, Pingfang Tao, Yongyu Cheng, Qiong Hu, Weijuan Huang, Yun Li, Zhihui Luo(), Guobao Huang()

Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, Yulin Normal University, Yulin, Guangxi 537000

Received:2022-04-27 Revised:2022-06-13 Published:2022-09-08
Contact: Zhihui Luo, Guobao Huang
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21961042); Basic Ability Improvement Project of Young and Middle-Aged Teachers in Guangxi Colleges(2021KY0587); Basic Ability Improvement Project of Young and Middle-Aged Teachers in Guangxi Colleges(2022KY0572); Program of Yulin Normal University(G2021ZK16); Program of Yulin Normal University(G2022ZK08)

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摘要/Abstract

不饱和烃(烯烃或炔烃)的双官能团化反应是引入一些官能团的重要策略, 也是合成多取代烃类化合物的重要方法, 在天然产物全合成及药物合成等领域被广泛应用. 综述了最近五年来电化学介导不饱和烃的双官能团化反应中的最新研究进展. 按照烯烃的双官能团化、不饱和烃的环化反应的分类介绍了电化学介导在不饱和烃的双官能团化反应中的应用及相关的反应机理, 为今后此类反应在有机合成中的应用提供参考.

关键词: 电化学, 烯烃/炔烃, 双官能团化

The difunctionalization of unsaturated hydrocarbons (alkenes or alkynes) is an important strategy to introduce functional groups, and is also an important method to synthesize polysubstituted hydrocarbons, which is widely used in the fields of total synthesis of natural products and drug synthesis. The latest research progress on the electrochemically enabled difunctionalization of alkenes or alkynes in recent five years is summarized. According to the classification of difunctionalization of alkenes and cyclization of unsaturated hydrocarbon, the application and the related reaction mechanism are introduced. It is hoped that this review can be referred to the future application in organic synthesis of electrochemic- mediated difunctionalization of alkenes/alkynes.

Key words: electrochemistry, alkenes/alkynes, difunctionalization

引用此文

李秀英, 陶萍芳, 程泳渝, 胡琼, 黄伟娟, 李芸, 罗志辉, 黄国保. 电化学促进的烯烃和炔烃双官能团化反应研究进展[J]. 有机化学, 2022, 42(12): 4169-4201.

Xiuying Li, Pingfang Tao, Yongyu Cheng, Qiong Hu, Weijuan Huang, Yun Li, Zhihui Luo, Guobao Huang. Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4169-4201.

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图/表 71

图式1. 电化学介导烯烃胺化三氟甲基化

Scheme 1. Electrochemically mediated trifluoromethylation of alkene amination

图式2. 电化学介导烯烃分子间氧化三氟甲基化和氨基三氟甲基化

Scheme 2. Electrochemically mediated intermolecular oxidative trifluoromethylation and amino trifluoromethylation of olefins

图式3. 电化学介导的烯烃的叠氮氧化

Scheme 3. Electrochemically mediated azide oxidation of alkenes

图式4. 电化学介导的缺电子烯烃的二氟甲基化反应

Scheme 4. Electrochemical difluoromethylation of electron-deficient alkenes

图式5. 电化学氧化烷氧磺酰化反应

Scheme 5. Electrochemical oxidative alkoxysulfonylation of alkenes

图式6. 电化学介导氧化炔烃/烯烃与磺酰肼反应

Scheme 6. Electrochemical oxidation-induced difunctionalization of alkynes and alkenes with sulfonyl hydrazides

图式7. 电化学介导的烯烃磺酰化/杂芳基化反应

Scheme 7. Electrochemical sulfonylation/heteroarylation of alkenes

图式8. 电化学介导的烯烃磺酰化反应

Scheme 8. Electrochemically mediated olefin sulfonylation

图式9. 电化学介导的烯烃的烷氧基磺化反应

Scheme 9. Electrochemically mediated alkoxy sulfonation of alkenes

图式10. 电化学介导的烯烃的胺化磺化反应

Scheme 10. Electrochemically mediated amination sulfonation of alkenes

图式11. 电化学介导的烯烃的磺化反应

Scheme 11. Electrochemically mediated sulfonation of alkenes

图式12. 电化学介导的烯烃甲酰氧基化反应

Scheme 12. Electrochemically mediated olefin formylation reaction

图式13. 电化学介导的烯烃氧酮化反应

Scheme 13. Electrochemically mediated oxyketonation of olefins

图式14. 电化学介导的烯烃羟基-炔化和-烯化反应

Scheme 14. Electrochemically enabled carbohydroxylation of alkenes

图式15. 烯烃二甲氧基化电化学反应

Scheme 15. Electrochemical dimethoxylation of olefins

图式16. 电化学介导的芳基乙烯合成酰亚胺化合物

Scheme 16. Electrochemical synthesis of aryl ethylene imides

图式17. 电化学介导的烯烃重氮化反应

Scheme 17. Electrochemical diazotization of alkenes

图式18. 烯烃的电化学邻二氯化反应

Scheme 18. Electrocatalytic radical dichlorination of alkenes

图式19. 电化学催化烯烃的氯烷基化反应

Scheme 19. Electrochemically catalyzed chloroalkylation of alkenes

图式20. 电化学介导苯乙烯衍生物的酰氧基化/三氟甲基化

Scheme 20. Electrochemically mediated acyloxylation/trifluoromethylation of styrene derivatives

图式21. 铜-电催化烯烃的二叠氮化

Scheme 21. Cu-electrocatalytic diazidation of alkenes

图式22. 脂肪族酮与烯烃的阴极区域选择性偶联

Scheme 22. Cathodic regioselective coupling of aliphatic ketones with alkenes

图式23. 脂肪族酮与烯烃的阴极区域选择性偶联

Scheme 23. Cathodic regioselective coupling of aliphatic ketones with alkenes

图式24. 焦亚硫酸钾与烯烃和醇的电化学多组分合成磺酸酯

Scheme 24. Electrochemical multi-component reaction of potassium metabisulfite with alkenes and alcohols enabling synthesis of sulfonate esters

图式25. 通过选择性电化学氯硫化或氯磺化氧化对未活化烯烃进行双官能化

Scheme 25. Difunctionalization of unactivated olefins via selective electrochemical chlorosulfuration or chlorosulfoxidation

图式26. 烯烃的可扩展电催化分子间酰氰化和氨基氰化

Scheme 26. Scalable electrocatalytic intermolecular acylcyanation and aminocyanation of alkenes

图式27. 电化学有机硒催化烯烃分子间氢唑基化

Scheme 27. Electrochemical organoselenium-catalyzed Intermolecular hydroazolylation of alkenes

图式28. 电化学介导苯乙烯衍生物的吲哚化

Scheme 28. Electrochemically mediated indolylation of styrene derivatives

图式29. 电化学介导烯烃衍生物碘化叠氮化

Scheme 29. Electrochemically mediated iodoazide of styrene derivatives

图式30. 烯烃的电化学氧化二氟化反应

Scheme 30. Electrochemical difluorination of alkenes

图式31. 电化学介导乙烯叠氮化合物合成双芳基硫胺和α-苯硫酮化合物

Scheme 31. Electrocatalytic synthesis of gem-bisarylthio enamines and α-phenylthio ketones

图式32. 电化学激活吲哚的磺酰化、酰肼化反应

Scheme 32. Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

图式33. 电化学介导烯烃与溴代芳烃反应

Scheme 33. Electroreductive carbofunctionalization of alkenes with alkyl bromides

图式34. 电化学构建氮杂环

Scheme 34. Electrochemical construction of nitrogen heterocycles

图式35. 电化学介导N-苯基酰胺烯烃合成γ-和δ-内酰胺化合物

Scheme 35. Electrochemically mediated synthesis of γ- and δ- lactam from N-phenylamide

图式36. N-芳基烯胺的电催化分子内脱氢环化反应

Scheme 36. Electrocatalytic intramolecular dehydrogenation cyclization of N-aryl enylamine

图式37. 丙烯酰胺的串联环化反应合成硒代吲哚酮类化合物

Scheme 37. Synthesis of selenoindolones by cyclization of acrylamide

图式38. 电化学介导末端烯发生双官能团硒化反应

Scheme 38. Electrochemically mediated bifunctional selenization of terminal alkenes

图式39. 电化学介导烯烃分子内氧化硒化/环化反应

Scheme 39. Electrochemical mediated intramolecular selenidation/cyclization of alkenes

图式40. 电化学锰催化1,6-烯炔化合物合成三氟氯甲基吡咯烷衍生物

Scheme 40. Synthesis of chlorotrifluoromethylated pyrrolidines by electrocatalytic radical ene-yne cyclization

图式41. 电化学介导的邻氨基烯烃自由基串联磺酰化环化反应

Scheme 41. Electrochemically mediated tandem sulfonylation cyclization of ortho-aminoalkene radicals

图式42. 电化学介导N-芳基丙烯酰胺的三氟甲基环化

Scheme 42. Electrochemically mediated trifluoromethyl cyclization of N-arylacrylamides

图式43. 电化学介导芳基丙烯酰胺三氟甲基化/C(sp2)—H官能团化

Scheme 43. Electrochemically mediated trifluoromethylation/ C(sp2)—H functionalization of arylacrylamides

图式44. 电化学介导烯醇三氟甲基化合成吗啉衍生物

Scheme 44. Electrochemically mediated enol trifluoromethylation to synthesize morpholine derivatives

图式45. 电化学介导烯醇三氟甲基化环化反应合成七元杂环

Scheme 45. Electrochemically mediated enol trifluoromethylation cyclization to synthesize seven-membered heterocycles

图式46. 电化学介导N-氰胺烯烃三氟甲基化环化

Scheme 46. Electrochemically mediated cyclization of N-cyanamide alkene trifluoromethylation

图式47. 电化学介导二苯基烯烃三氟甲基化环化

Scheme 47. Electrochemically mediated difluoromethylation cyclization of diphenylalkenes

图式48. 电化学磺酰化诱导的烯烃内酯化: 磺酰邻苯二甲酸酯的合成

Scheme 48. Electrochemical sulfonylation-induced lactonization of alkenes: synthesis of sulfonyl phthalides

图式49. 钴循环电催化烯烃的氧化加氢功能化反应

Scheme 49. Electrocatalytic oxidative hydrofunctionalization reactions of alkenes via Co-cycle

图式50. 电化学杂芳胺内炔烃[3+2]环化合成咪唑并N-杂芳香化合物

Scheme 50. Electrochemically enabled synthesis of imidazo-fused N—Heteroaromatic compounds through (3+2) annulation reaction of heteroarylamines with intramolecular alkynes

图式51. 电化学介导C—H/N—H官能团化合成(氮杂)吲哚

Scheme 51. Electrochemically mediated C—H/N—H functionalization synthesis of (aza)indole

图式52. 电化学条件下的乙炔基雌二醇衍生物的修饰

Scheme 52. Modification of ethinylestradiol derivatives under electrochemical conditions

图式53. 电化学合成苯并噁唑酮衍生物

Scheme 53. Electrochemical synthesis of benzoxazolone derivatives

图式54. 电化学合成苯并噁唑酮及其后续转化

Scheme 54. Electrochemical synthesis of benzoxazolones and their subsequent transformations

图式55. 炔酮和烯酮与亚磺酸电氧化串联环化合成磺化茚酮化合物

Scheme 55. Electrooxidative tandem cyclization of activated alkynes with sulfinic acids to sulfonated indenones

图式56. 邻硝基苯乙炔电化学合成2,1-苯并噁唑化合物

Scheme 56. Electrochemically enabled synthesis of 2,1-ben- zoxazoles from o?nitrophenylacetylenes

图式57. 电化学介导炔烃发生自由基串联环化反应

Scheme 57. Electrochemically mediated radical tandem cyclization of alkynes

图式58. 电化学介导1,6-烯炔氧化-环加成合成含氮杂环化合物

Scheme 58. Electrosynthesis of azaheterocycles through anodic oxidation cyclization of 1,6-enynes

图式59. 电化学介导三芳基取代烯烃与氨基磺酸甲酯合成氮丙啶化合物

Scheme 59. Electrochemically mediated synthesis of aziridine from triaryl-substituted alkenes and sulfamate

图式60. 烯烃与1,2-或1,3-二醇的电化学脱氢环化反应

Scheme 60. Electrochemical dehydrogenation cyclization of alkenes with 1,2- or 1,3-diol

图式61. 乙烯/乙炔与芳基/乙烯酰胺电化学合成异喹啉酮类衍生物

Scheme 61. Electrochemical synthesis of isoquinolone derivatives from ethylene/acetylene and aryl/vinyl amides

图式62. 电化学介导烯烃与叔苯胺[4+2]环化合成四氢喹啉类化合物

Scheme 62. Electrochemically mediated cyclization of alkenes with tertiary aniline [4+2] to form tetrahydroquinoline

图式63. 电化学介导烯烃与2-氨基苯甲酰胺官能团化合成喹唑啉酮类化合物

Scheme 63. Electrochemical synthesis of quinazolinones from alkenes and 2-aminobenzamides

图式64. 电化学氧化邻胺基苯乙烯、二氧化碳、二级胺的三组分反应

Scheme 64. Three-component reaction of electrochemical oxidation of o-aminostyrene, carbon dioxide and secondary amine

图式65. 电化学介导的N-2-吡啶酰肼与内炔烃的环化反应

Scheme 65. Electrochemically mediated cyclization of N-2-pyridyl hydrazine with inner alkynes

图式66. 钌/电化学脱氢炔烃环化反应

Scheme 66. Ruthenium/electrochemical dehydroalkyne cyclization

图式67. 电化学介导的芳基乙醛酸与内炔烃的脱羧[4+2]环化反应

Scheme 67. Electrochemical mediated decarboxylation [4+2] of aryl glyoxylic acid with inner alkynes

图式68. 炔烃和1,3二羰基化合物[4+2]电化学环化合成1-萘酚

Scheme 68. Synthesis of 1?naphthols by intermolecular annulation of alkynes with 1,3-dicarbonyl compounds

图式69. 电化学介导酰胺和烯烃脱氢偶联

Scheme 69. Electrochemically mediated dehydrogenation coupling of amides and alkenes

图式70. 烯烃/炔烃电化学氧化[4+2]环化合成多环芳香化合物

Scheme 70. Electrochemical oxidative [4+2] annulation for the unfunctionalized heterobiaryl compounds

图式71. 一锅两步电化学合成邻二氮萘衍生物

Scheme 71. One-pot two-step electrosynthesis of cinnoline derivatives

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电化学促进的烯烃和炔烃双官能团化反应研究进展

Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes

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