自由基介导含氟杂环化合物的构建研究

doi:10.6023/cjoc202109033

摘要/Abstract

含氟杂环化合物由于其优异的物理化学性质, 在有机化学、药物化学、材料科学等诸多领域扮演着重要的角色. 但自然界中, 天然含氟杂环化合物屈指可数, 开发高效的含氟杂环化合物的合成方法显得尤为重要. 随着过渡金属催化、光催化以及电催化自由基反应的迅速发展, 自由基化学在合成领域取得了突破性进展, 激发了有机化学家利用自由基化学构建含氟杂环的兴趣. 主要以不饱和烃的单氟烷基化、二氟烷基化、三氟甲基化、三氟烷氧/硫/硒基化、全氟烷基化以及杂环的直接C—H氟烷基化进行分类, 从过渡金属催化、光催化以及电催化等几个方面, 对自由基介导的含氟侧链杂环化合物的构建进行讨论.

关键词: 自由基, 含氟杂环, 金属催化, 光催化, 电催化

Fluoro-containing heterocyclics play an important role in many fields, such as organic chemistry, pharmaceutical chemistry and material science due to their excellent physical and chemical properties. However, there are few natural fluoro-containing heterocyclics in nature, so it is particularly important to develop efficient synthesis methods of fluoro- containing heterocyclics. With the rapid development of transition metal catalyzed, photocatalyzed and electrocatalyzed radical reactions, radical chemistry has made a breakthrough in the field of synthesis and stimulated the interest of organic chemists in constructing fluoro-containing heterocyclics by using radical chemistry. In this paper, monofluoroalkylation, difluoroalkylation, trifluoromethylation, trifluoroalkoxy/sulfur/selenylation, perfluoroalkylation of unsaturated hydrocarbons and direct C—H fluoroalkylation of heterocycles are classified, and the construction of fluorine-containing side chain heterocycles mediated by free radicals is discussed from the aspects of transition metal catalysis, photocatalysis and electrocatalysis.

Key words: radical, fluorinated heterocycle, metal catalysis, photocatalytic, electrocatalysis

引用此文

陈宁, 雷佳, 王智传, 刘颖杰, 孙凯, 唐石. 自由基介导含氟杂环化合物的构建研究[J]. 有机化学, 2022, 42(4): 1061-1084.

Ning Chen, Jia Lei, Zhichuan Wang, Yingjie Liu, Kai Sun, Shi Tang. Construction of Fluoro-containing Heterocycles Mediated by Free Radicals[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1061-1084.

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图/表 80

图式1. N-芳基丙烯酰胺的单氟甲基化反应

Scheme 1. Monofluoromethylation of N-arylacrylamides

图式2. 单氟甲基化香豆素的合成及反应机理

Scheme 2. Synthesis and mechanism of CH2F-containing coumarins

图式3. Pd催化烯烃的分子内芳基二氟甲基化反应

Scheme 3. Pd-catalyzed intramolecular aryldifluoromethylation of alkenes

图式4. ICF2CO2Et与1,6-烯炔的二氟甲基化反应

Scheme 4. Difluoromethylation of ICF2CO2Et with 1,6-enyne

图式5. 3-和2-炔丙基酰胺取代的吲哚的二氟甲基化反应

Scheme 5. Difluoromethylation of 3-propargylamide-substituted and 2-propargylamide-substituted indoles and α-bromodifluoroacetamides

图式6. 炔烃和α-溴二氟乙酰胺的氨基二氟烷基化反应

Scheme 6. Aminodifluoroalkylation of alkynes and α-bromodi- fluoroacetamides

图式7. 炔烃和α-溴二氟乙酰胺的氨基二氟烷基化反应机理

Scheme 7. Mechanism for aminodifluoroalkylation of alkynes and α-bromodifluoroacetamides

图式8. 二氟化吡咯里西啶和吲哚里西啶的合成

Scheme 8. Synthesis of difluorinated pyrrolizidines and indolizidines

图式9. ICF2COOEt与N-炔丙基酰胺的二氟甲基化反应

Scheme 9. Difluoromethylation of ICF2COOEt with N-pro- pargylamide

图式10. 不饱和羧酸的氧二氟烷基化反应

Scheme 10. Oxydifluoroalkylation of unsaturated carboxylic acids

图式11. 钴催化炔烃环己二烯酮的二氟烷基化

Scheme 11. Cobalt-catalyzed difluoroalkylation of alkyne-tethered cyclohexadienones

图式12. 二氟烷基化苯并呋喃、苯并噻吩和吲哚衍生物的合成

Scheme 12. Synthesis of difluoroalkylated benzofuran, benzothiophene, and indole derivatives

图式13. 铜催化烯烃的硒二氟甲基化反应

Scheme 13. Cu-catalyzed selenodifluoromethylation of alkenes

图式14. 铜催化烯烃的硒二氟甲基化反应机理

Scheme 14. Mechanism for Cu-catalyzed selenodifluoromethylation of alkenes

图式15. 二氟烷基化1-茚酮的合成

Scheme 15. Synthesis of difluoroalkylated 1-indenones

图式16. 铜催化烯炔的溴二氟乙酰化环化反应

Scheme 16. Copper-catalyzed bromodifluoroacetylative cyclization of enynes

图式17. 异氰化物的自由基(苯磺酰)二氟甲基化反应

Scheme 17. Radical (phenylsulfonyl)difluoromethylation of isocyanides

图式18. 碱促进的1,6-烯炔二氟甲基化反应

Scheme 18. Base promoted difluoromethylation of 1,6-enynes

图式19. BrCF2CO2Et与苯炔酸酯的芳基二氟乙酰化反应

Scheme 19. Aryldifluoroacetylation of phenyl alkynoates with BrCF2CO2Et

图式20. 烯烃与溴二氟乙酰胺的氨基二氟烷基化反应

Scheme 20. Aminodifluoroalkylation of alkenes with bromodifluoroacetamides

图式21. 可见光介导的游离苯胺的二氟烷基化-酰胺化

Scheme 21. Visible-light-mediated difluoroalkylation-amidation of free anilines

图式22. 偕-二氟螺环-γ-内酰胺-辛二醇的合成

Scheme 22. Synthesis of gem-difluorinated spiro-γ-lactam oxindoles

图式23. 吲哚衍生物的连续二氟甲基化脱芳构化、羟基化和取代反应

Scheme 23. Sequential difluoromethylative dearomatization, hydroxylation, and substitution of indole derivatives

图式24. 二氟乙酰化苯并二氢吡喃-4-酮的合成

Scheme 24. Synthesis of difluoroacetylated chroman-4-ones

图式25. 二氟乙酰化苯并二氢吡喃-4-酮的合成机理

Scheme 25. Mechanism for synthesis of difluoroacetylated chroman-4-ones

图式26. 3-二氟烷基化香豆素的合成

Scheme 26. Synthesis of 3-CF2-containing coumarins

图式27. 二氟甲基化2-羟吲哚和喹啉-2,4-二酮的合成

Scheme 27. Synthesis of difluoromethylated 2-oxindoles and quinoline-2,4-diones

图式28. 二氟甲基化2-羟吲哚的合成机理

Scheme 28. Mechanism for synthesis of difluoromethylated 2-oxindoles

图式29. CF2HSO2NHNHBoc与炔烃的二氟甲基芳基化反应

Scheme 29. Difluoromethylarylation reaction of CF2HSO2NHNHBoc with alkynes

图式30. CF2HSO2NHNHBoc与炔烃的二氟甲基芳基化反应机理

Scheme 30. Mechanism for difluoromethylarylation reaction of CF2HSO2NHNHBoc with alkynes

图式31. 含二氟甲基的内酯的合成

Scheme 31. Synthesis of CF2H-containing lactones

图式32. 电催化氟烷基化/环化/吲哚氧化裂解反应

Scheme 32. Electrocatalytic fluoroalkylation/cyclization/indole oxidative cleavage reaction

图式33. 电催化氟烷基化/环化/吲哚氧化裂解反应机理

Scheme 33. Mechanism of electrocatalytic fluoroalkylation/cyclization/indole oxidative cleavage reaction

图式34. 三氟乙基异喹啉的合成

Scheme 34. Synthesis of trifluoroethyl isoquinolines

图式35. 三氟甲基化1'H-螺[吖嗪-2,4'-喹啉]-2'(3'H)-酮的合成

Scheme 35. Synthesis of trifluoromethyl-containing 1'H-spiro-[azirine-2,4'-quinolin]-2'(3'H)-ones

图式36. 三氟甲基化1,8-萘啶的合成

Scheme 36. Synthesis of trifluoromethyl-containing 1,8-naph- thyridines

图式37. 2,2,2-三氟乙基噁唑、噁唑啉和呋喃的合成

Scheme 37. Synthesis of 2,2,2-trifluoroethyl oxazoles, oxazolines and furans

图式38. 全取代三氟甲基吡咯的一锅合成

Scheme 38. One-pot synthesis of fully-substituted trifluoroethyl pyrroles

图式39. 全取代三氟甲基吡咯的一锅合成反应机理

Scheme 39. Mechanism for one-pot synthesis of fully-substituted trifluoromethyl pyrroles

图式40. α-苄基化甲苯磺酰甲基异氰化物衍生物和Togni试剂的反应

Scheme 40. Reaction of α-benzylated tosylmethyl isocyanide derivatives with Togni reagent

图式41. 苯系1,7-烯炔的光诱导自由基三氟甲基碘化

Scheme 41. Photoinduced radical trifluoromethyliodation of benzene-tethered 1,7-enyne

图式42. 2-乙炔基苯磺酰胺与Togni试剂的光诱导三氟甲基化

Scheme 42. Photoinduced trifluoromethylation of 2-ethynylben- zenesulfonamide with Togni’s reagent

图式43. 含三氟甲基杂环化合物的合成

Scheme 43. Synthesis of CF3-containing heterocyclic compounds

图式44. 1,7-烯炔的溴三氟甲基化

Scheme 44. Bromo-trifluoromethylation of 1,7-enynes

图式45. N-苯甲酰胺的三氟甲基化

Scheme 45. Trifluoromethylation of N-benzamides

图式46. 三氟甲基化二苯并[b,e]氮杂?的合成

Scheme 46. Synthesis of trifluoromethylated dibenz[b,e]azepine

图式47. 1,7-烯炔的三氟甲基化/环化

Scheme 47. Trifluoromethylation/cyclization of 1,7-enynes

图式48. 1,7-烯炔的三氟甲基化/环化反应机理

Scheme 48. Mechanism for trifluoromethylation/cyclization of 1,7-enynes

图式49. 光催化氮烯转移反应

Scheme 49. Photocatalytic nitrene transfer reactions

图式50. 氯三氟甲基化吡咯烷的合成

Scheme 50. Synthesis of chlorotrifluoromethylated pyrrolidines

图式51. N-芳基丙烯酰胺电化学三氟甲基/环化

Scheme 51. Electrochemical trifluoromethylation/cyclization of N-arylacrylamides

图式52. 锰介导的氮杂环电化学三氟甲基化

Scheme 52. Mn-Mediated electrochemical trifluoromethylation of azaheterocycles

图式53. 与氮相连接的烯-6-醇分子内三氟甲基化

Scheme 53. Intramolecular trifluoromethylation of N-tethered alken-6-ols

图式54. 与氮相连接的烯-6-醇分子内三氟甲基化反应机理

Scheme 54. Mechanism for intramolecular trifluoromethylation of N-tethered alken-6-ols

图式55. 环状N-磺酰亚胺的三氟甲基化

Scheme 55. Trifluoromethylation of cyclic N-sulfonylimines

图式56. 乙烯基叠氮化物的电化学串联氟烷基化/环化

Scheme 56. Electrochemical tandem fluoroalkylation/cycli- zation of vinyl azides

图式57. 含CF3和SCF3的吲哚[2,1-a]异喹啉-6(5H)-酮的合成

Scheme 57. Synthesis of CF3- and SCF3-containing indolo[2,1-a]isoquinolin-6(5H)-ones

图式58. (杂)芳烃的三氟甲氧基化反应

Scheme 58. Trifluoromethoxylation of (hetero)arenes

图式59. 含SCF3的苯并噁嗪和噁唑啉的合成

Scheme 59. Synthesis of SCF3-containing benzoxazines and oxazolines

图式60. N-(邻氰基二芳基)丙烯酰胺的三氟甲硫基化反应

Scheme 60. Trifluoromethylthiolation of N-(o-cyanobiaryl)acrylamides

图式61. 三氟甲硫基取代的色氨酸的合成

Scheme 61. Synthesis of trifluoromethylthio-substituted tryptanthrins

图式62. 可见光介导的吲哚三氟甲基硒化

Scheme 62. Visible-light-mediated trifluoromethylselenolation of indoles

图式63. (杂)芳烃与双(三氟甲基)过氧化物的三氟甲氧基化反应

Scheme 63. Trifluoromethoxylation of (hetero)arenes with bis(trifluoromethyl)peroxide

图式64. 全氟异喹啉二酮的合成

Scheme 64. Synthesis of perfluorinated isoquinolinediones

图式65. 甲基丙烯酰苯甲酰胺与全氟烷基碘化物的反应

Scheme 65. Reaction of methacryloyl benzamides with perfluoroalkyl iodides

图式66. 全氟烷基化嘧啶的三组分[3+2+1]杂环化合成

Scheme 66. Three-component [3+2+1] heteroannulation for synthesis of perfluoroalkylated pyrimidine

图式67. 全氟烷基化2H-氮杂丙烯啶的合成

Scheme 67. Synthesis of perfluoroalkylated 2H-azirines

图式68. 全氟烷基化苯并咪唑并[2,1-α]异喹啉-6(5H)-酮和吲哚并[2,1-α]异喹啉-6(5H)-酮的合成

Scheme 68. Synthesis of perfluoroalkylated benzimidazo[2,1- α]isoquinoline-6(5H)-ones and indolo[2,1-α]isoquinolin-6(5H)-ones

图式69. 全氟烷基化苯并咪唑并[2,1-α]异喹啉-6(5H)-酮的合成反应机理

Scheme 69. Mechanism for synthesis of perfluoroalkylated benzimidazo[2,1-α]isoquinoline-6(5H)-ones

图式70. 全氟烷基异噁唑的四组分[2+1+1+1]环化合成反应

Scheme 70. The four-component [2+1+1+1] cyclization synthesis of perfluoroalkyl isoxazoles

图式71. 杂芳烃底物的C—H二氟甲基化反应

Scheme 71. C—H Difluoromethylation of heteroarene substrates

图式72. 电化学和TBHP自由基引发下三氟甲基化的比较

Scheme 72. Comparison of trifluoromethylation under electrochemical and TBHP radical initiation

图式73. 溴离子介导的缺电子杂环的三氟甲基化

Scheme 73. Trifluoromethylation of electron-deficient heterocycles mediated by bromide ions

图式74. (杂)芳烃的镍催化全氟烷基化

Scheme 74. Ni-catalyzed perfluoroalkylation with of (hetero)arenes

图式75. (杂)芳烃的光电化学C—H三氟甲基化

Scheme 75. Electrophotochemical C—H trifluoromethylation of (hetero)arenes

图式76. (杂)芳烃的光电化学C—H三氟甲基化反应机理

Scheme 76. Mechanism for electrophotochemical C—H trifluoromethylation of (hetero)arenes

图式77. 吲哚衍生物的电化学氟烷基化

Scheme 77. Electrochemical fluoroalkylation of indole derivatives

图式78. 铜催化香豆素与氟代烷基溴化物的C—H二氟烷基化

Scheme 78. Copper-catalyzed C—H difluoroalkylation of coumarins with fluoroalkyl bromides

图式79. (杂)芳烃的交流电解三氟甲基化

Scheme 79. Alternating current electrolytic trifluoromethylation of (hetero)arenes

图式80. 咪唑并[1,2-α]吡啶和全氟烷基碘化物的全氟烷基化反应

Scheme 80. Perfluoroalkylation of the imidazo[1,2-α]pyridines with perfluoroalkyl iodides

参考文献 86

[1]	Schlosser, M. Angew. Chem., nt. Ed. 2006, 45, 5432.
[2]	Liu, Y.-J.; Han, Y.-H.; Lin, L.-Q.; Xu, Y. Chin. J. Org. Chem. 2021, 41, 934. (in Chinese)
	( 刘颖杰, 韩莹徽, 林立青, 许颖, 有机化学, 2021, 41, 934.)
[3]	Chen, B.-Q.; Ge, D.-H.; Wang, X.; Chu, X.-Q. Chin. J. Org. Chem. 2021, 41, 1925. (in Chinese)
	( 程步清, 葛丹华, 汪欣, 褚雪强, 有机化学, 2021, 41, 1925.)
[4]	Wang, S.-W.; Yu, J.; Zhou, Q.-Y.; Chen, S.-Y.; Xu, Z.-Y.; Tang, S. ACS Sustainable Chem. Eng. 2019, 7, 10154.
[5]	Tang, S.; Yuan, L.; Deng, Y.-L.; Li, Z.-Z.; Wang, L.-N.; Huang, G.-X.; Sheng, R.-L. Tetrahedron Lett. 2017, 58, 2127.
[6]	Du, K.-Y.; Zhang, Z.-M.; Sheng, W.-J. Chin. J. Org. Chem. 2021, 41, 3242. (in Chinese)
	( 杜科莹, 张展铭, 盛卫坚, 有机化学, 2021, 41, 3242.)
[7]	Wang, X.; Lei, J.; Liu, Y.-J.; Ye, Y.; Li, J.-Z.; Sun, K. Org. Chem. Front. 2021, 8, 2079. doi: 10.1039/D0QO01629B
[8]	Pan, J.; Wu, J.-J.; Wu, F.-H. Chin. J. Org. Chem. 2021, 41, 983. (in Chinese)
	( 潘军, 吴晶晶, 吴范宏, 有机化学, 2021, 41, 983.)
[9]	Zou, Z.-L.; Zhang, W.-G.; Wang, Y.; Pan, Y. Org. Chem. Front. 2021, 8, 2786. doi: 10.1039/D1QO00054C
[10]	Tang, X.; Thomoson, C. S.; Dolbier Jr., W. R. Org. Lett. 2014, 16, 4594. doi: 10.1021/ol502163f
[11]	Fu, W.-J.; Sun, Y.-N.; Li, X.-Y. Synth. Commun. 2020, 50, 388. doi: 10.1080/00397911.2019.1697452
[12]	Wang, J.-Y.; Su, Y.-M.; Yin, F.; Bao, Y.; Zhang, X.; Xu, Y.-M.; Wang, X.-S. Chem. Commun. 2014, 50, 4108. doi: 10.1039/C3CC49315F
[13]	Wang, Y.-Q.; He, Y.-T.; Zhang, L.-L.; Wu, X.-X.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2015, 17, 4280. doi: 10.1021/acs.orglett.5b02068
[14]	Hua, H.-L.; Zhang, B.-S.; He, Y.-T.; Qiu, Y.-F.; Hu, J.-Y.; Yang, Y.-C.; Liang, Y.-M. Chem. Commun. 2016, 52, 10396. doi: 10.1039/C6CC05745D
[15]	Lv, Y.-H.; Pu, W.-Y.; Chen, Q.; Wang, Q.-Q.; Niu, J.-J.; Zhang, Q. J. Org. Chem. 2017, 82, 8282. doi: 10.1021/acs.joc.7b01313
[16]	Zhou, L.; Hossain, M.-L.; Xiao, T. Chem. Rec. 2016, 16, 319-334. doi: 10.1002/tcr.201500228
[17]	Wang, X.-Y.; Li, M.; Yang, Y.-Y.; Guo, M.-J.; Tang, X.-Y.; Wang, G.-W. Adv. Synth. Catal. 2018, 360, 2151. doi: 10.1002/adsc.201701643
[18]	Ma, J.-W.; Wang, Q.; Wang, X.-G.; Liang, Y.-M. J. Org. Chem. 2018, 83, 13296. doi: 10.1021/acs.joc.8b02111
[19]	Da, Y.; Han, S.-N.; Du, X.-Y.; Liu, S.-D.; Liu, L.; Li, J. Org. Lett. 2018, 20, 5149.
[20]	Han, S.-N.; Liu, S.-D.; Ackermann, L.; Li, J. Org. Lett. 2019, 21, 5387. doi: 10.1021/acs.orglett.9b01400
[21]	Zhang, P.-B.; Wang, C.; Cui, M.-C.; Du, M.-S.; Li, W.-W.; Jia, Z.-X.; Zhao, Q. Org. Lett. 2020, 22, 1149.
[22]	Sun, K.; Wang, S.-N.; Feng, R.-R.; Zhang, Y.-X.; Wang, X.; Zhang, Z.-G.; Zhang, B. Org. Lett. 2019, 21, 2052. doi: 10.1021/acs.orglett.9b00240
[23]	Lv, Y.-H.; Pu, W.-Y.; Wang, Q.-Q.; Chen, Q.; Niu, J.-J.; Zhang, Q. Adv. Synth. Catal. 2017, 359, 3114. doi: 10.1002/adsc.201700559
[24]	Shen, Z.-J.; Wang, S.-C.; Hao, W.-J.; Yang, S.-Z.; Tu, S.-J.; Jiang, B. Adv. Synth. Catal. 2019, 361, 1. doi: 10.1002/adsc.201801478
[25]	Zhu, S.-Q.; Yang, H.-B.; Jiang, A.-L.; Zhou, B.; Han, Y.; Yan, C.-G.; Shi, Y.-C.; Hou, H. J. Org. Chem. 2020, 85, 15667. doi: 10.1021/acs.joc.0c02114
[26]	Xiao, P.; Rong, J.; Ni, C.-F.; Guo, J.-K.; Li, X.-J.; Chen, D.-B.; Hu, J.-B. Org. Lett. 2016, 18, 5912. pmid: 27934497
[27]	Li, M.; Wang, C.-T.; Qiu, Y.-F.; Zhu, X.-Y.; Han, Y.-P.; Xia, Y.; Li, X.-S.; Liang, Y.-M. Chem. Commun. 2018, 54, 5334. doi: 10.1039/C8CC03280G
[28]	Fu, W.-J.; Zhu, M.; Zou, G.-L.; Xu, C.; Wang, Z.-Q.; Ji, B.-M. J. Org. Chem. 2015, 80, 4766. doi: 10.1021/acs.joc.5b00305
[29]	Zhang, M.-L.; Li, W.-P.; Duan, Y.-Q.; Xu, P.; Zhang, S.-L.; Zhu, C.-J. Org. Lett. 2016, 18, 3266. doi: 10.1021/acs.orglett.6b01515
[30]	Yu, L.-C.; Gu, J.-W.; Zhang, S.; Zhang, X.-G. J. Org. Chem. 2017, 82, 3943. doi: 10.1021/acs.joc.7b00111
[31]	Wang, Q.; Qu, Y.; Xia, Q.; Song, H.-J.; Song, H.-B.; Liu, Y.-X.; Wang, Q.-M. Chem.-Eur. J. 2018, 24, 11283.
[32]	Wang, Q.; Qu, Y.; Liu, Y.-X.; Song, H.-B.; Wang, Q.-M. Adv. Synth. Catal. 2019, 361, 4739. doi: 10.1002/adsc.201900755
[33]	Zhou, N.-N.; Wu, M.-X.; Zhang, M.; Zhou, X.-Q. Asian J. Org. Chem. 2019, 8, 828. doi: 10.1002/ajoc.201900121
[34]	Chen, Y.-T.; Shu, C.-Y.; Luo, F.; Xiao, X.-H.; Zhu, H.-H. Chem. Commun. 2018, 54, 5373. doi: 10.1039/C8CC02636J
[35]	Song, D.; Wang, C.-M.; Ye, Z.-P.; Xia, P.-J.; Deng, Z.-X.; Xiao, J.-A.; Xiang, H.-Y.; Yang, H. J. Org. Chem. 2019, 84, 7480. doi: 10.1021/acs.joc.9b00715 pmid: 31062593
[36]	Sun, H.; Jiang, Y.; Yang, Y.-S.; Li, Y.-Y.; Li, L.; Wang, W.-X.; Feng, T.; Li, Z.-H.; Liu, J.-K. Org. Biomol. Chem. 2019, 17, 6629. doi: 10.1039/C9OB01213C
[37]	Xiong, P.; Xu, H.-H.; Song, J.-S.; Xu, H.-C. J. Am. Chem. Soc. 2018, 140, 2460. doi: 10.1021/jacs.8b00391 pmid: 29406700
[38]	Guo, J.-Y.; Wu, R.-X.; Jin, J.-K.; Tian, S.-K. Org. Lett. 2016, 18, 3850. doi: 10.1021/acs.orglett.6b01862
[39]	Taniguchi, T.; Idota, A.; Ishibashi, H. Org. Biomol. Chem. 2011, 9, 3151. doi: 10.1039/c0ob01119c pmid: 21437319
[40]	Zhang, S.; Li, L.-J.; Zhang, J.-J.; Zhang, J.-Q.; Xue, M.-Y.; Xu, K. Chem. Sci. 2019, 10, 3181. doi: 10.1039/C9SC00100J
[41]	Yuan, X.; Cui, Y.-S.; Zhang, X.-P.; Qin, L.-Z.; Sun, Q.; Duan, X.; Chen, L.; Li, G.-G.; Qiu, J.-K.; Guo, K. Chem.-Eur. J. 2021, 27, 6522.
[42]	Bhaskaran, R. P.; Babu, B. P. Adv. Synth. Catal. 2020, 362, 5219. doi: 10.1002/adsc.202000996
[43]	Liu, K.; Chen, S.; Li, X.-G.; Liu, P.-N. J. Org. Chem. 2016, 81, 265. doi: 10.1021/acs.joc.5b01995
[44]	Meng, Q.; Chen, F.; Yu, W.; Han, B. Org. Lett. 2017, 19, 5186. doi: 10.1021/acs.orglett.7b02453
[45]	Li, J.-J.; Lei, Y.-F.; Yu, Y.; Qin, C.; Fu, Y.-W.; Li, H.; Wang, W. Org. Lett. 2017, 19, 6052.
[46]	Dong, J.-J.; Zhang, S.-L. Adv. Synth. Catal. 2020, 362, 795. doi: 10.1002/adsc.201901405
[47]	Ge, J.-Y.; Ding, Q.-P.; Wang, X.-H.; Peng, Y.-Y. J. Org. Chem. 2020, 85, 7658. doi: 10.1021/acs.joc.9b03470
[48]	Zhou, X.; Huang, C.; Zeng, Y.; Xiong, J.; Xiao, Y.; Zhang, J. Chem. Commun. 2017, 53, 1084. doi: 10.1039/C6CC09595J
[49]	Wang, L.; Studer, A. Org. Lett. 2017, 19, 5701. doi: 10.1021/acs.orglett.7b02882 pmid: 28976201
[50]	An, Y.-Y.; Kuang, Y.-Y.; Wu, J. Org. Chem. Front. 2016, 3, 994. doi: 10.1039/C6QO00267F
[51]	Xiang, Y.-C.; Kuang, Y.-Y.; Wu, J. Org. Chem. Front. 2016, 3, 901. doi: 10.1039/C6QO00120C
[52]	Han, H. S.; Oh, E. H.; Jung, Y. S.; Han, S. B. Org. Lett. 2018, 20, 1698. doi: 10.1021/acs.orglett.8b00648
[53]	Yuan, X.; Zheng, M.-W.; Di, Z.-C.; Cui, Y.-S.; Zhuang, K.-Q.; Qin, L.-Z.; Fang, Z. Qiu, J.-K.; Li, G.-G.; Guo, K. Adv. Synth. Catal. 2019, 361, 1835. doi: 10.1002/adsc.201801681
[54]	Wang, S.-W.; Dai, P.; Yan, Z.-C.; Wang, Y.-J.; Shao, J.-X.; Wu, Y.-H.; Deng, C.; Zhang, W.-H. ChemistrySelect 2019, 4, 10329. doi: 10.1002/slct.201902545
[55]	Qi, X.-K.; Zhang, H.; Pan, Z.-T.; Liang, R.-B.; Zhu, C.-M.; Li, J.-H.; Tong, Q.-X.; Gao, X.-W.; Wu, L.-Z.; Zhong, J.-J. Chem. Commun. 2019, 55, 10848. doi: 10.1039/C9CC04977K
[56]	Zhuang, K.-Q.; Cui, Y.-S.; Yuan, X.; Qin, L.-Z.; Sun, Q.; Duan, X.; Chen, L.; Zhang, X.-P.; Qiu, J.-K.; Guo, K. ACS Sustainable Chem. Eng. 2020, 8, 11729. doi: 10.1021/acssuschemeng.0c03745
[57]	Guo, Y.-J.; Pei, C.; Jana, S.; Koenigs, R. M. ACS Catal. 2021, 11, 337. doi: 10.1021/acscatal.0c04564
[58]	Ye, K.-Y.; Song, Z.-D.; Sauer, G. S.; Harenberg, J. H.; Fu, N.-K.; Lin, S. Chem.-Eur. J. 2018, 24, 12274.
[59]	Jiang, Y.-Y.; Dou, G.-Y.; Xu, K.; Zeng, C.-C. Org. Chem. Front. 2018, 5, 2573. doi: 10.1039/C8QO00645H
[60]	Zhang, Z.-X.; Zhang, L.; Cao, Y.; Li, F.; Bai, G.-C.; Liu, G.-Q.; Yang, Y.; Mo, F.-Y. Org. Lett. 2019, 21, 762. doi: 10.1021/acs.orglett.8b04010
[61]	Claraz, A.; Courant, T.; Masson, G. Org. Lett. 2020, 22, 1580. doi: 10.1021/acs.orglett.0c00176
[62]	Li, Z.; Jiao, L.-C.; Sun, Y.-H.; He, Z.-Y.; Wei, Z.-L.; Liao, W.-W. Angew. Chem., nt. Ed. 2020, 59, 7266.
[63]	Lin, L.; Liang, Q.; Kong, X.-Q.; Chen, Q.-J.; Xu, B. J. Org. Chem. 2020, 85, 15708. doi: 10.1021/acs.joc.0c02213
[64]	Fuentes, N.; Kong, W.-Q.; Fernández-Sánchez, L.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2015, 137, 964. doi: 10.1021/ja5115858
[65]	Zheng, W.-J.; Morales-Rivera, C. A.; Lee, J. W.; Liu, P.; Ngai, M. Y. Angew. Chem., nt. Ed. 2018, 130, 9793. doi: 10.1002/ange.201800598
[66]	Zheng, W.-J.; Lee, J. W.; Morales-Rivera, C. A.; Liu, P.; Ngai, M. Y. Angew. Chem., nt. Ed. 2018, 57, 13795.
[67]	Zhu, M.; Li, R.-X.; You, Q.-Q.; Fu, W.-J.; Guo, W.-S. Asian J. Org. Chem. 2019, 8, 2002. doi: 10.1002/ajoc.201900499
[68]	Zhu, M.; Fu, W.-J.; Guo, W.-S.; Tian, Y.-F.; wang, Z.-Q.; Ji, B.-M. Org. Biomol. Chem. 2019, 17, 3374. doi: 10.1039/C9OB00342H
[69]	Guo, J.-C.; Hao, Y.-N.; Li.; Wang, Z.-W.; Liu, Y.-X.; Li, Y.-Q.; Wang, Q.-M. Org. Biomol. Chem. 2020, 18, 1994. doi: 10.1039/D0OB00233J
[70]	Zordo-Banliat, A. D.; Barthélémy, L.; Bourdreux, F.; Tuccio, B.; Dagousset, G.; Pégot, B.; Magnier, E. Eur. J. Org. Chem. 2020, 2020, 506.
[71]	Dix, S.; Golz, P.; Schmid, J. R.; Riedel, S.; Hopkinson, M. N. Chem.-Eur. J. 2021, 27, 11554.
[72]	Tang, S.; Deng, Y.-L.; Li, J.; Wang, W.-X.; Ding, G.-L.; Wang, M.-W.; Xiao, Z.-P.; Wang, Y.-C.; Sheng, R.-L. J. Org. Chem. 2015, 80, 12599 doi: 10.1021/acs.joc.5b01803 pmid: 26580021
[73]	Deng, Y.-L.; Tang, S.; Ding, G.-L.; Wang, M.-W.; Li, J.; Li, Z.-Z.; Yuan, L.; Sheng, R.-L. Org. Biomol. Chem. 2016, 14, 9348. doi: 10.1039/C6OB01550F
[74]	Chu, X.-Q.; Xie, T.; Li, L.; Ge, D.-H.; Shen, Z.-L.; Loh, T. P. Org. Lett. 2018, 20, 2749. doi: 10.1021/acs.orglett.8b00963
[75]	Xiong, H.-G.; Ramkumar, N.; Chiou, M.-F.; Jian, W.-J.; Li, Y.-J.; Su, J.-H.; Zhang, X.-H.; Bao, H.-L. Nat. Commun. 2019, 10, 1. doi: 10.31413/nativa.v10i1.11824
[76]	Zeng, F.-L.; Sun, K.; Chen, X.-L.; Yuan, X.-Y.; He, S.-Q.; Liu, Y.; Peng, Y.-Y.; Qu, L.-B.; Lv, Q.-Y.; Yu, B. Adv. Synth. Catal. 2019, 361, 1. doi: 10.1002/adsc.201801478
[77]	Chen, Y.-J.; Li, L.-K.; He, X.; Li, Z.-P. ACS Catal. 2019, 9, 9098. doi: 10.1021/acscatal.9b03189
[78]	Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494. doi: 10.1021/ja211422g pmid: 22229949
[79]	O'Brien, A. G.; Maruyama, A.; Inokuma, Y.; Fujita, M.; Baran, P. S.; Blackmond, D. G. Angew. Chem., nt. Ed. 2014, 53, 1.
[80]	Dou, G.-Y.; Jiang, Y.-Y.; Xu, K.; Zeng, C.-C. Org. Chem. Front. 2019, 6, 2392. doi: 10.1039/C9QO00552H
[81]	Zhang, S.-K.; Nicolas, R. L.; Weniger, F.; Rabeah, J.; Neumann, H.; Taeschler, C.; Beller, M. Chem. Commun. 2019, 55, 6723. doi: 10.1039/C9CC01971E
[82]	Qiu, Y.; Scheremetjew, A.; Finger, L. H.; Ackermann, L. Chem.- Eur. J. 2020, 26, 3241.
[83]	Hossain, M. J.; Ono, T.; Wakiya, K.; Hisaeda, Y. Chem. Commun. 2017, 53, 10878. doi: 10.1039/C7CC06221D
[84]	Rao, M.; Fan, Z.-W.; Yuan, Y.-F.; Cheng, J.-J. ChemCatChem 2020, 12, 5256. doi: 10.1002/cctc.202001025
[85]	Rodrigo, S.; Um, C.; Mixdorf, J. C.; Gunasekera, D.; Nguyen, H. M.; Luo, L. Org. Lett. 2020, 22, 6719. doi: 10.1021/acs.orglett.0c01906
[86]	Huang, J.-B.; Wu, D.-D.; Bai, X.-K.; Cai, P.-Y.; Zhu, W.-G. New J. Chem. 2021, 45, 4925. doi: 10.1039/D1NJ00651G