通过环化反应构建多取代咪唑的最新研究进展

doi:10.6023/cjoc202107014

摘要/Abstract

咪唑是一类非常重要的五元含氮杂环化合物, 在有机合成化学中具有广泛的用途, 其广泛存在于天然产物、应用药物和材料等领域中, 而且也是一类重要的有机合成中间体, 因此合成咪唑的方法也倍受人们的关注. 归纳总结了通过环化反应构建多取代咪唑的最新研究进展, 主要介绍了以肟酯、2H-氮杂环丙烯、酮类化合物、2-氨基吡啶、叠氮化合物、三唑类化合物、炔类化合物、异硫氰酸酯、芳胺类化合物、脒类化合物和腈类化合物等作为起始原料合成咪唑类化合物的方法及研究进展, 并展望了它的发展前景.

关键词: 咪唑, 环化, 合成, 研究进展

Imidazoles are a class of very important 5-memeric nitrogen-containing heterocyclic compounds, which have a wide range of applications in organic synthetic chemistry. They are widely found in natural products, applied drugs, materials and other fields, and are also a class of important organic synthesis intermediates. Therefore, the synthetic method of imidazole has attracted much attention. The recent progress in the synthesis of polysubstituted imidazoles by cyclization reaction is summarized. These methods and research progress of the synthesis of imidazoles from oxime esters, 2H-azacyclopropenes, ketones, 2-aminopyridines, azides, triazoles, alkynes, isothiocyanates, aromatic amines, amidines and nitriles are reviewed. Finally, the prospects of the reaction with this reagent are also proposed.

Key words: imidazole, cyclization, synthesis, research process

引用此文

赵咪娜, 杨梓墨, 杨得锁. 通过环化反应构建多取代咪唑的最新研究进展[J]. 有机化学, 2022, 42(1): 111-128.

Mina Zhao, Zimo Yang, Desuo Yang. Recent Progress in Synthesis of Polysubstituted Imidazoles by Cyclization Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 111-128.

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图/表 61

图1. 一些重要的咪唑化合物

Figure 1. Some important imidazoles

图式1. 肟酯和乙烯基叠氮化物合成咪唑

Scheme 1. Synthesis of imidazole from oxime acetates and vinyl azides

图式2. 肟酯和四氢异喹啉合成咪唑的机理

Scheme 2. Plausible mechanism for the synthesis of imidazole from ketoxime acetates and tetrahydroisoquinolines

图式3. 由N-苯基偕胺肟酯合成咪唑

Scheme 3. Synthesis of imidazole from N-phenyl amidoxime esters

图式4. 苯甲亚胺酸乙酯和2H-氮杂环丙烯合成咪唑的机理

Scheme 4. Plausible mechanism for the synthesis of imidazole from benzimidates and 2H-azirines

图式5. 硝酮和2H-氮杂环丙烯合成咪唑的机理

Scheme 5. Plausible mechanism for the synthesis of imidazole with nitrones and 2H-azirines

图式6. 2-氯吡啶和2H-氮杂环丙烯合成咪唑

Scheme 6. Synthesis of imidazole from 2-chloropyridines and 2H-azirines

图式7. 邻苯二胺和β-二酮合成咪唑

Scheme 7. Synthesis of imidazole from o-phenylenediamines and β-diketones

图式8. 2-氨基-1,3,5-三嗪和1,3-二羰基化合物合成咪唑

Scheme 8. Synthesis of imidazole from 2-amino-1,3,5-triazines with 1,3-dicarbonyl compounds

图式9. 由1,2-二酮合成咪唑

Scheme 9. Synthesis of imidazole from 1,2 diketone

图式10. α-亚甲基酮、芳香醛和乙酸铵合成咪唑

Scheme 10. Synthesis of imidazole from α-methylene ketone, benzaldehyde and NH4OAc

图式11. α-亚甲基酮和醛合成咪唑

Scheme 11. Synthesis of imidazole from α-methylene ketone and aldehydes

图式12. 由芳基酮和苄胺合成咪唑

Scheme 12. Synthesis of imidazole from benzylamines and aryl ketones

图式13. 芳基酮和醛合成咪唑

Scheme 13. Synthesis of imidazole from aryl ketones and aldehyde

图式14. 芳基甲基酮、2-氨基苯甲醇和TosMIC合成咪唑的机理

Scheme 14. Plausible mechanism for the synthesis of imidazole from aryl methyl ketones, 2-aminobenzyl alcohols and TosMIC

图式15. 芳基酮、苄胺和胺合成咪唑

Scheme 15. Synthesis of imidazole from aryl ketones, benzylamine and amine

图式16. 查尔酮和胺合成咪唑

Scheme 16. Synthesis of imidazole from chalcones and amine

图式17. 2-氨基吡啶和酮合成咪唑

Scheme 17. Synthesis of imidazole from 2-aminopyridine and ketones

图式18. 2-氨基吡啶和醛合成咪唑

Scheme 18. Synthesis of imidazole from 2-aminopyridines and aldehydes

图式19. 1,3-二羰基化合物和2-氨基吡啶合成咪唑

Scheme 19. Synthesis of imidazole from 1,3-dicarbonyls and 2-aminopyridines

图式20. 苯甲脒盐酸盐和乙烯基叠氮合成咪唑的机理

Scheme 20. Plausible mechanism for the synthesis of imidazole from benzimidamides and vinyl azides

图式21. 炔丙基叠氮化合物、异氰酸酯和胺合成咪唑

Scheme 21. Synthesis of imidazole from propargylazide derivatives, isocyanates and amines

图式22. 甲苯酰甲基叠氮化合物和L-脯氨酸合成咪唑

Scheme 22. Synthesis of imidazole from phenacyl azides with L-proline

图式23. 芳基叠氮化合物和TosMIC合成咪唑

Scheme 23. Synthesis of imidazole from aryl azides and TosMIC

图式24. 乙烯基叠氮化合物和氨基腈合成咪唑

Scheme 24. Synthesis of imidazole from vinyl azides and cyanamide

图式25. 乙烯基叠氮化合物和亚胺合成咪唑

Scheme 25. Synthesis of imidazole from vinyl azides and imines

图式26. 腈和N-(全)氟烷基取代的1,2,3-三唑合成咪唑

Scheme 26. Synthesis of imidazole from nitrile and N-(per)- fluoroalkyl-1,2,3-triazoles

图式27. 胺、炔烃和TMSN3合成咪唑的机理

Scheme 27. Plausible mechanism for the synthesis of imidazole from amines, alkynes and TMSN3

图式28. 噁二唑酮和炔酰胺合成咪唑

Scheme 28. Synthesis of imidazole from oxadiazolones with ynamides

图式29. 炔烃、2-氨基氮杂环和苄基/烯丙基溴化物合成咪唑

Scheme 29. Synthesis of imidazole from alkyne, 2-amino-N- heterocycle, benzyl or allylic bromide

图式30. 炔烃和2-氨基吡啶合成咪唑

Scheme 30. Synthesis of imidazole from alkyne and 2-amino- pyridine

图式31. N-吡啶磺酰亚胺和炔酰胺合成咪唑

Scheme 31. Synthesis of imidazole from N-pyridinyl sulfilimines and ynamide

图式32. 炔烃、腈和叔丁基醚合成咪唑的机理

Scheme 32. Plausible mechanism for the synthesis of imidazole from alkynes, nitriles and tBuOK

图式33. 芳基异硫氰酸酯合成咪唑的机理

Scheme 33. Plausible mechanism for the synthesis of imidazole from aryl isothiocyanates

图式34. 伯醇和邻苯二胺合成咪唑

Scheme 34. Synthesis of imidazole from primary alcohol and o-phenylenediamines

图式35. 由邻苯二胺合成咪唑

Scheme 35. Synthesis of imidazole from o-phenylenediamines

图式36. 邻硝基苯胺和醇合成咪唑的机理

Scheme 36. Plausible mechanism for the synthesis of imidazole from o-nitroanilines and alcohols

图式37. 邻苯二胺和D-葡萄糖合成咪唑

Scheme 37. Synthesis of imidazole from o-phenylenediamines and D-glucose

图式38. 邻苯二胺和苯腈合成咪唑

Scheme 38. Synthesis of imidazole from o-phenylenediamines and benzonitriles

图式39. 由脒合成咪唑

Scheme 39. Synthesis of imidazole from amidines

图式40. N-苯基苄脒和苯乙醛合成咪唑的机理

Scheme 40. Plausible mechanism for the synthesis of imidazole from N-phenylbenzamidine with phenylacetaldehyde

图式41. 炔基苯并碘酮和脒肟合成咪唑

Scheme 41. Synthesis of imidazole from alkynylbenziodoxolones and amidoximes

图式42. 脒和炔醛合成咪唑

Scheme 42. Synthesis of imidazole from amidines and ynals

图式43. 脒、炔醛和醇/酚/水合成咪唑

Scheme 43. Synthesis of imidazole from amidines, ynals and alcohols, phenols, or water

图式44. 脒、炔醛和羧酸或胺合成咪唑

Scheme 44. Synthesis of imidazole from amidines, ynals and carboxylic acids or amines

图式45. 脒、炔醛和硼酸合成咪唑

Scheme 45. Synthesis of imidazole from amidines, ynals and boronic acids

图式46. 脒、炔醛和磺酸钠合成咪唑

Scheme 46. Synthesis of imidazole from amidines, ynals and sodium sulfinates

图式47. 脒、炔醛和水合成咪唑

Scheme 47. Synthesis of imidazole from amidines, ynals and water

图式48. 由酰胺合成咪唑的机理

Scheme 48. Plausible mechanism for the synthesis of imidazole from amides

图式49. 甘氨酸衍生物和5-烷氧基噁唑合成咪唑

Scheme 49. Synthesis of imidazole from glycine derivatives and 5-alkoxyoxazoles

图式50. 由N-烷基烯胺合成咪唑

Scheme 50. Synthesis of imidazole from N-alkyl enamines

图式51. 烯胺和碘合成咪唑盐

Scheme 51. Synthesis of imidazolium salts from enamines and iodine

图式52. 由烯胺合成咪唑的机理

Scheme 52. Plausible mechanism for the synthesis of imidazole from enamines

图式53. 由烯胺和胺合成咪唑

Scheme 53. Synthesis of imidazole from enamines and amines

图式54. 硼酸和N-取代的2-氨基乙腈合成咪唑

Scheme 54. Synthesis of imidazole from boronic acids and N- substituted-2-amino-acetonitriles

图式55. 苄胺和腈合成咪唑

Scheme 55. Synthesis of imidazole from benzylamines and ntriles

图式56. 亚甲胺叶立德和异腈合成咪唑

Scheme 56. Synthesis of imidazole from azomethine ylides and isocyanides

图式57. 异腈、2,2,2-三氟重氮乙烷和活化的亚甲基异腈或亚甲胺叶立德合成咪唑

Scheme 57. Synthesis of imidazole from isocyanides, 2,2,2- trifluorodiazoethane and activated methylene isocyanides or azomethine ylides

图式58. 活性亚甲基异腈和乙烯酮亚胺合成咪唑

Scheme 58. Synthesis of imidazole from active methylene isocyanides and ketenimines

图式59. 多环芳香亚甲胺叶立德和腈合成咪唑

Scheme 59. Synthesis of imidazole from polycyclic aromatic azomethine ylides and nitriles

图式60. 胺和ClCF2COONa合成咪唑的机理

Scheme 60. Plausible mechanism for the synthesis of imidazole from amines and ClCF2COONa

参考文献 78

[1]	(a) Roue, M.; Domart-Coulon, I.; Ereskovsky, A.; Djediat, C.; Perez, T.; Bourguet-Kondracki, M.-L. J. Nat. Prod. 2010, 73, 1277. doi: 10.1021/np100175x pmid: 23740514
	(b) Zhang, L.; Peng, X.-M.; Damu, G. L. V.; Geng, R.-X.; Zhou, C.-H. Med. Res. Rev. 2014, 34, 340. doi: 10.1002/med.21290 pmid: 23740514
[2]	(a) Tang, W.-Z.; Yang, Z.-Z.; Wu, W.; Tang, J.; Sun, F.; Wang, S.-P.; Cheng, C.-W.; Yang, F.; Lin, H.-W. J. Nat. Prod. 2018, 81, 894. doi: 10.1021/acs.jnatprod.7b01006
	(b) Zhao, K.; Yu, F.; Liu, W.; Huang, Y.; Said, A. A.; Li, Y.; Zhang, Q. J. Org. Chem. 2020, 85, 101. doi: 10.1021/acs.joc.9b02156
	(c) Qiu, Z.-P.; Tan, J.-H.; Cai, N.; Wang, K.; Ji, S.-M.; Huo, Y.-P. Chin. J. Org. Chem. 2019, 39, 679. (in Chinese) doi: 10.6023/cjoc201807007
	(邱志鹏, 谭继华, 蔡宁, 王凯, 籍少敏, 霍延平, 有机化学, 2019, 39, 679.) doi: 10.6023/cjoc201807007
[3]	Rohrig, U. F.; Majjigapu, S. R.; Chambon, M.; Bron, S.; Pilotte, L.; Colau, D.; Van den Eynde, B. J.; Turcatti, G.; Vogel, P.; Zoete, V.; Michielin, O. Eur. J. Med. Chem. 2014, 84, 284. doi: 10.1016/j.ejmech.2014.06.078
[4]	Perchellet, E. M.; Perchellet, J.-P.; Baures, P. W. J. Med. Chem. 2005, 48, 5955. pmid: 16161999
[5]	Atwell, G. J.; Fan, J.-Y.; Tan, K.; Denny, W. A. J. Med. Chem. 1998, 41, 4744. pmid: 9822545
[6]	Choi, J. Y.; Plummer, M. S.; Starr, J.; Desbonnet, C. R.; Soutter, H.; Chang, J.; Richard Miller, J.; Dillman, K.; Miller, A. A.; Roush, W. R. J. Med. Chem. 2012, 55, 852. doi: 10.1021/jm201349f
[7]	Vlahakis, J. Z.; Lazar, C.; Crandall, I. E.; Szarek, W. A. Bioorg. Med. Chem. 2010, 18, 6184.
[8]	Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M. J.; Richard Keys, J.; Land vatter, S. W.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. Nature 1994, 372, 739. doi: 10.1038/372739a0
[9]	Hojabri, L.; Hartikka, A.; Moghaddam, F. M.; Arvidsson, P. I. Adv. Synth. Catal. 2007, 349, 740. doi: 10.1002/(ISSN)1615-4169
[10]	Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667. doi: 10.1021/cr010338r
[11]	Mao, P.; Yang, L.-R.; Xiao, Y.-M.; Yuan, J.-W.; Mai, W.-P.; Gao, J.; Zhang, X.-C. Chin. J. Org. Chem. 2019, 39, 443. (in Chinese) doi: 10.6023/cjoc201807008
	(毛璞, 杨亮茹, 肖咏梅, 袁金伟, 买文鹏, 高杰, 张心持, 有机化学, 2019, 39, 443.) doi: 10.6023/cjoc201807008
[12]	Hindi, K. M.; Panzner, M. J.; Tessier, C. A.; Cannon, C. L.; Youngs, W. J. Chem. Rev. 2009, 109, 3859. doi: 10.1021/cr800500u
[13]	Radziszewski, B. Ber. Dtsch. Chem. Ges. 1882, 15, 1493. doi: 10.1002/cber.v15:2
[14]	Zhao, X.-Y.; Ding, Y.-Y.; Lü, Y.-T.; Kang, C.-M. Chin. J. Org. Chem. 2019, 39, 1304. (in Chinese) doi: 10.6023/cjoc201809034
	(赵鑫雨, 丁扬扬, 吕英涛, 康从民, 有机化学, 2019, 39, 1304.)
[15]	Yang, K.; Yao, C.; Gao, J.-J.; Chen, S.-H.; Zheng, X.-J.; Deng, L.-X.; Zhang, Y.-N.; Liu, M.-J.; Wang, Z.-Y. Chin. J. Org. Chem. 2020, 40, 4168. (in Chinese) doi: 10.6023/cjoc202005074
	(杨凯, 姚辰, 高娟娟, 陈思鸿, 郑雪洁, 邓璐璇, 张毓娜, 刘美娟, 汪朝阳, 有机化学, 2020, 40, 4168.) doi: 10.6023/cjoc202005074
[16]	Xu, X.-M.; Chen, D.-M.; Wang, Z.-L. Chin. J. Org. Chem. 2019, 39, 3338. (in Chinese) doi: 10.6023/cjoc201904068
	(徐鑫明, 陈德茂, 王祖利, 有机化学, 2019, 39, 3338.) doi: 10.6023/cjoc201904068
[17]	Huang, H.; Ji, X.; Tang, X.; Zhang, M.; Li, X.; Jiang, H. Org. Lett. 2013, 15, 6254. doi: 10.1021/ol403105p
[18]	Zhu, Z.; Tang, X.; Li, J.; Li, X.; Wu, W.; Deng, G.; Jiang, H. Org. Lett. 2017, 19, 1370. doi: 10.1021/acs.orglett.7b00203
[19]	Qu, Z.; Zhang, F.; Deng, G.-J.; Huang, H. Org. Lett. 2019, 21, 8239. doi: 10.1021/acs.orglett.9b02978
[20]	Li, G.; He, R.; Liu, Q.; Wang, Z.; Liu, Y.; Wang, Q. J. Org. Chem. 2019, 84, 8646. doi: 10.1021/acs.joc.9b01158
[21]	Shi, S.; Xu, K.; Jiang, C.; Ding, Z. J. Org. Chem. 2018, 83, 14791. doi: 10.1021/acs.joc.8b02437
[22]	Angyal, A.; Demjen, A.; Wolfling, J.; Puskas, L. G.; Kanizsai, I. J. Org. Chem. 2020, 85, 3587. doi: 10.1021/acs.joc.9b03288 pmid: 32020808
[23]	Vuillermet, F.; Bourret, J.; Pelletier, G. J. Org. Chem. 2021, 86, 388. doi: 10.1021/acs.joc.0c02148 pmid: 33269922
[24]	Miao, C.; Hou, Q.; Wen, Y.; Han, F.; Li, Z.; Yang, L.; Xia, C.-G. ACS Sustainable Chem. Eng. 2019, 7, 12008.
[25]	Pan, Z.; Song, C.; Zhou, W.; Cui, D.-M.; Zhang, C. New J. Chem. 2020, 44, 6182. doi: 10.1039/C9NJ05794C
[26]	Adhikary, S.; Majumder, L.; Pakrashy, S.; Srinath, R.; Mukherjee, K.; Mandal, C.; Banerji, B. ACS Omega 2020, 5, 14394. doi: 10.1021/acsomega.0c00934 pmid: 32596577
[27]	Jayram, J.; Jeena, V. Green Chem. 2017, 19, 5841. doi: 10.1039/C7GC02484C
[28]	Jayram, J.; Jeena, V. RSC Adv. 2018, 8, 37557. doi: 10.1039/C8RA07238H
[29]	Huang, H.; Ji, X.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2013, 355, 170. doi: 10.1002/adsc.201200582
[30]	Chen, X.; Wang, Z.; Huang, H.; Deng, G.-J. Adv. Synth. Catal. 2018, 360, 4017. doi: 10.1002/adsc.v360.20
[31]	Toledo, I.; Grigolo, T. A.; Bennett, J. M.; Elkins, J. M.; Pilli, R. A. J. Org. Chem. 2019, 84, 14187. doi: 10.1021/acs.joc.9b01844 pmid: 31460764
[32]	Geng, X.; Wang, C.; Huang, C.; Bao, Y.; Zhao, P.; Zhou, Y.; Wu, Y.-D.; Feng, L.-L.; Wu, A.-X. Org. Lett. 2020, 22, 140. doi: 10.1021/acs.orglett.9b04060
[33]	Zeng, L.; Li, J.; Gao, J.; Huang, X.; Wang, W.; Zheng, X.; Gu, L.; Li, G.; Zhang, S.; He, Y. Green Chem. 2020, 22, 3416. doi: 10.1039/D0GC00375A
[34]	Salfeena, C. T. F.; Jalaja, R.; Davis, R.; Suresh, E.; Somappa, S. B. ACS Omega 2018, 3, 8074. doi: 10.1021/acsomega.8b01017
[35]	Bhagat, S. B.; Telvekar, V. N. Tetrahedron Lett. 2017, 58, 3662. doi: 10.1016/j.tetlet.2017.08.017
[36]	Tan, J.; Ni, P.; Huang, H.; Deng, G.-J. Org. Biomol. Chem. 2018, 16, 4227. doi: 10.1039/C8OB00981C
[37]	Roslan, I. I.; Ng, K.-H.; Jaenicke, S.; Chuah, G.-K. Catal. Sci. Technol. 2019, 9, 1528. doi: 10.1039/C9CY00141G
[38]	Reddy, N. N. K.; Rao, S. N.; Ravi, C.; Adimurthy, S. ACS Omega 2017, 2, 5235. doi: 10.1021/acsomega.7b00969
[39]	Xiong, J.; Wei, X.; Liu, Z.-M.; Ding, M.-W. J. Org. Chem. 2017, 82, 13735. doi: 10.1021/acs.joc.7b02606 pmid: 29148765
[40]	Reddy, C. N.; Sathish, M.; Adhikary, S.; Nanubolu, J. B.; Alarifi, A.; Maurya, R. A.; Kamal, A. Org. Biomol. Chem. 2017, 15, 2730. doi: 10.1039/C7OB00299H
[41]	Necardo, C.; Alfano, A. I.; Grosso, E. D.; Pelliccia, S.; Galli, U.; Novellino, E.; Meneghetti, F.; Giustiniano, M.; Tron, G. C. J. Org. Chem. 2019, 84, 16299. doi: 10.1021/acs.joc.9b02546
[42]	Man, L.; Copley, R. C. B.; Handlon, A. Org. Biomol. Chem. 2019, 17, 6566. doi: 10.1039/C9OB01100E
[43]	Zhu, Z.; Lin, H.; Liang, B.; Huang, J.; Liang, W.; Chen, L.; Huang, Y.; Chen, X.; Li, Y. Chem. Commun. 2020, 56, 5621. doi: 10.1039/C9CC10042C
[44]	Motornov, V.; Markos, A.; Beier, P. Chem. Commun. 2018, 54, 3258. doi: 10.1039/C8CC01446A
[45]	Arepally, S.; Babu, V. N.; Bakthadoss, M.; Sharada, D. S. Org. Lett. 2017, 19, 5014. doi: 10.1021/acs.orglett.7b01840 pmid: 28901153
[46]	Zhao, Y.; Hu, Y.; Li, X.; Wan, B. Org. Biomol. Chem. 2017, 15, 3413. doi: 10.1039/C7OB00701A
[47]	Li, X.; Wang, T.; Lu, Y.-J.; Ji, S.; Huo, Y.; Liu, B. Org. Biomol. Chem. 2018, 16, 7143. doi: 10.1039/C8OB01532E
[48]	He, Q.-X.; Liang, Y.-F.; Xu, C.; Yao, X.-K.; Cao, H.; Yao, H.-G. ACS Comb. Sci. 2019, 21, 149. doi: 10.1021/acscombsci.8b00149
[49]	Tian, X.; Song, L.; Rudolph, M.; Wang, Q.; Song, X.; Rominger, F.; Hashmi, A. S. K. Org. Lett. 2019, 21, 1598. doi: 10.1021/acs.orglett.9b00140
[50]	Wang, Q.; Chen, X.; Wang, X.-G.; Liu, H.-C.; Liang, Y.-M. Org. Lett. 2019, 21, 9874. doi: 10.1021/acs.orglett.9b03782
[51]	Geng, X.; Liu, S.; Wang, W.; Qu, J.; Wang, B. J. Org. Chem. 2020, 85, 12635. doi: 10.1021/acs.joc.0c01806
[52]	Li, L.; Luo, Q.; Cui, H.; Li, R.; Zhang, J.; Peng, T. ChemCatChem 2018, 10, 1607. doi: 10.1002/cctc.v10.7
[53]	Senadi, G. C.; Kudale, V. S.; Wang, J.-J. Green Chem. 2019, 21, 979. doi: 10.1039/C8GC03839B
[54]	Das, S.; Mallick, S.; Sarkar, S. D. J. Org. Chem. 2019, 84, 12111. doi: 10.1021/acs.joc.9b02090
[55]	Raja, D.; Philips, A.; Palani, P.; Lin, W.-Y.; Devikala, S.; Senadi, G. C. J. Org. Chem. 2020, 85, 11531. doi: 10.1021/acs.joc.0c01053
[56]	Lin, M.; Wu, F.; Liu, T.-H.; Chen, Z.-T.; Xu, X.-Z.; Ke, F. Chin. J. Org. Chem. 2020, 40, 2563. (in Chinese) doi: 10.6023/cjoc202004016
	(林媚, 吴凡, 刘天惠, 陈志涛, 许秀枝, 柯方, 有机化学, 2020, 40, 2563.) doi: 10.6023/cjoc202004016
[57]	Zhao, H.-B.; Hou, Z.-W.; Liu, Z.-J.; Zhou, Z.-F.; Song, J.; Xu, H.-C. Angew. Chem., Int. Ed. 2017, 56, 587. doi: 10.1002/anie.201610715
[58]	Wang, J.; Zhang, F.-D.; Tang, D.; Wu, P.; Zhang, X.-G.; Chen, B.-H. RSC Adv. 2017, 7, 24594. doi: 10.1039/C7RA01966A
[59]	Li, M.; Li, W.; Lin, C.-D.; Wang, J.-H.; Wen, L.-R. J. Org. Chem. 2019, 84, 6904. doi: 10.1021/acs.joc.9b00659
[60]	Wang, C.; Jiang, H.; Chen, W.; Dong, J.; Chen, Z.; Cao, H. Org. Biomol. Chem. 2017, 15, 6463. doi: 10.1039/C7OB01242J
[61]	Wang, C.; Wang, E.; Chen, W.; Zhang, L.; Zhan, H.; Wu, Y.; Cao, H. J. Org. Chem. 2017, 82, 9144. doi: 10.1021/acs.joc.7b01781
[62]	Wang, C.; Lai, J.; Chen, C.; Li, X.; Cao, H. J. Org. Chem. 2017, 82, 13740. doi: 10.1021/acs.joc.7b02612
[63]	Wang, C.; Yu, Y.; Su, Z.; Li, X.; Cao, H. Org. Lett. 2019, 21, 4420. doi: 10.1021/acs.orglett.9b00969
[64]	Liu, W.; Zhang, Y.; He, J.; Yu, Y.; Yuan, J.; Ye, X.; Zhang, Z.; Xue, L.; Cao, H. J. Org. Chem. 2019, 84, 11348. doi: 10.1021/acs.joc.9b01818
[65]	Liu, W.; He, J.; Liu, X.; Yu, Y.; Pei, Y.; Zhu, B.; Cao, H. J. Org. Chem. 2020, 85, 14954. doi: 10.1021/acs.joc.0c01715
[66]	Mauro, G. D.; Maryasin, B.; Kaiser, D.; Shaaban, S.; Gonzalez, L.; Maulide, N. Org. Lett. 2017, 19, 3815. doi: 10.1021/acs.orglett.7b01678
[67]	Xie, J.; Huang, Y.; Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2017, 19, 6056. doi: 10.1021/acs.orglett.7b02767
[68]	Ma, H.; Zhang, X.; Chen, L.; Yu, W. J. Org. Chem. 2017, 82, 11841. doi: 10.1021/acs.joc.7b01361
[69]	Xia, B.; Chen, W.; Zhao, Q.; Yu, W.; Chang, J. Org. Lett. 2019, 21, 2583. doi: 10.1021/acs.orglett.9b00541
[70]	Xu, K.; Yang, R.; Yang, S.; Jiang, C.; Ding, Z. Org. Biomol. Chem. 2019, 17, 8977. doi: 10.1039/C9OB01895F
[71]	Wang, W.; Zhang, S.; Shi, G.; Chen, Z. Org. Biomol. Chem. 2021, 19, 6682. doi: 10.1039/D1OB00942G
[72]	Yu, H.; Xiao, L.; Yang, X.; Shao, L. Chem. Commun. 2017, 53, 9745. doi: 10.1039/C7CC05315K
[73]	Das, U. K.; Shimon, L. J. W.; Milstein, D. Chem. Commun. 2017, 53, 13133. doi: 10.1039/C7CC08322J
[74]	Huang, X.; Cong, X.; Mi, P.; Bi, X. Chem. Commun. 2017, 53, 3858. doi: 10.1039/C7CC00772H
[75]	Yu, Y.; Zhang, Y.; Wang, Z.; Liang, Y.-X.; Zhao, Y.-L. Org. Chem. Front. 2019, 6, 3657. doi: 10.1039/C9QO00856J
[76]	Cai, J.; Bai, H.; Wang, Y.; Xu, X.; Xie, H.; Liu, J. Chem. Commun. 2019, 55, 3821. doi: 10.1039/C9CC01257E
[77]	Li, Q.-Q.; Ochiai, K.; Lee, C.-A.; Ito, S. Org. Lett. 2020, 22, 6132. doi: 10.1021/acs.orglett.0c02203
[78]	Wang, Y.; Zhou, Y.; Song, Q. Chem. Commun. 2020, 56, 6106. doi: 10.1039/D0CC01919D