直接三氟甲硒基化反应研究进展

doi:10.6023/cjoc202206050

摘要/Abstract

三氟甲硒基化反应是近几年继三氟甲硫基化反应后的又一重要研究课题, 由于三氟甲硒基同时包含氟和硒这两种重要的化学元素, 并且含三氟甲硒基的化合物具有重要的潜在生物活性, 因此近年来越来越多的科研工作者开始把目光转向这一新兴基团. 此综述按照亲核三氟甲硒基化反应、亲电三氟甲硒基化反应、自由基三氟甲硒基化反应三种反应类型, 对近6年来的国内外学者在直接三氟甲硒基化反应的研究进行了全面总结, 并对部分反应机理进行详细的论述, 最后对直接三氟甲硒基化反应进行了总结和展望.

关键词: 三氟甲硒基, 亲核反应, 亲电反应, 自由基反应

The trifluoromethylselenylation reaction is another important research topic after trifluoromethylsulfanylation reaction in recent years. Because the trifluoromethylselenyl group contains two important chemical elements, fluorine and selenium, and the compounds containing trifluoromethyl selenide have important potential biological activities, more and more researchers begin to turn their attention to this new group in recent years. In this paper, according to the three reaction types of nucleophilic trifluoromethylselenylation reaction, electrophilic trifluoromethylselenylation reaction and radical trifluoromethylselenylation reaction, the research results of domestic and foreign scholars on direct trifluoromethylselenylation reaction in recent 6 years are comprehensively summarized, and some reaction mechanisms are discussed in detail. Finally, the direct trifluoromethylselenylation reaction is summarized and prospected.

Key words: trifluoromethylseleno, nucleophilic reaction, electrophilic reaction, radical reaction

引用此文

胡朝明, 吴纪红, 吴晶晶, 吴范宏. 直接三氟甲硒基化反应研究进展[J]. 有机化学, 2023, 43(1): 36-56.

Zhaoming Hu, Jihong Wu, Jingjing Wu, Fanhong Wu. Research Progress on Direct Trifluoromethylselenylation[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 36-56.

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图/表 44

图式1. 镍催化的芳基卤化物的三氟甲硒基化反应

Scheme 1. Nickel-catalyzed trifluoromethylselenylation of aryl halides

图式2. 使用Me4NSeCF3进行无催化剂和无添加剂的三氟甲基硒化反应

Scheme 2. Catalyst-free and additive-free trifluoromethylselenation using Me4NSeCF3

图式3. 双核镍催化芳基碘与Me4NSeCF3交叉偶联反应

Scheme 3. Binuclear nickel-catalyzed cross-coupling reaction of aryl iodide with Me4NSeCF3

图式4. CaCl2促进醇与Me4NSeCF3的脱羟基三氟甲基硒化反应

Scheme 4. CaCl2 promotes dehydroxytrifluoromethylselenation of alcohols with Me4NSeCF3

图式5. 未活化烯烃的Markovnikov型三氟甲硒基化反应

Scheme 5. Markovnikov-type trifluoromethylselenylation of unactivated alkenes

图式6. 铜催化的烯烃自由基1,2-三氟甲基硒化反应

Scheme 6. Copper-catalyzed radical 1,2-trifluoromethylselenation of alkenes

图式7. 金氧化还原催化芳基卤化物三氟甲硒基化反应

Scheme 7. Gold redox catalyzed trifluoromethylselenylation of aryl halides

图式8. 一种铜介导的α-三氟甲硒基酮的合成方法

Scheme 8. A kind of synthetic method of copper-mediated α-trifluoromethylselenyl ketone

图式9. 合成三氟甲硒基吡喃酮类衍生物

Scheme 9. Synthesis of trifluoromethylselenopyrone derivatives

图式10. 三组分二氟烷基三氟甲硒基化合物的合成

Scheme 10. Synthesis of three-component difluoroalkyl trifluoromethylselenyl compounds

图式11. α-重氮酸酯参与的高效合成α-三氟甲硒基酯

Scheme 11. Efficient synthesis of α-trifluoromethylselenyl esters involved by α-diazoate

图式12. 钯催化串联合成三氟甲硒基苯并呋喃衍生物

Scheme 12. Tandem synthesis of trifluoromethylselenylbenzofuran derivatives catalyzed by palladium

图式13. TDAE介导的无金属催化的亲核三氟甲硒基化反应

Scheme 13. TDAE-mediated metal-free nucleophilic trifluoromethylselenylation

图式14. 碘介导的无金属催化的亲核三氟甲硒基化反应

Scheme 14. Iodine-mediated metal-free nucleophilic trifluoromethylselenylation

图式15. 铁介导的无金属催化的亲核三氟甲硒基化反应

Scheme 15. Iron-mediated metal-free nucleophilic trifluoromethylselenylation

图式16. 电催化活化卤代烷三氟甲硒基化反应

Scheme 16. Electrocatalytic activation of alkyl halides for trifluoromethylselenylation

图式17. AgSeCF3参与的C(sp3)—H的三氟甲硒基化反应

Scheme 17. Trifluoromethylselenylation of C(sp3)—H involved by AgSeCF3

图式18. BT-SeCF3参与的醇脱氧三氟甲硒基化反应

Scheme 18. Deoxytrifluoromethylselenylation of alcohols with BT-SeCF3

图式19. TsSeCF3参与的铜催化苯硼酸的三氟甲硒基化反应

Scheme 19. Copper-catalyzed trifluoromethylselenylation of phenylboronic acid involved by TsSeCF3

图式20. 端炔与TsSeCF3亲电三氟甲硒基化反应

Scheme 20. Electrophilic trifluoromethylselenylation of terminal alkynes with TsSeCF3

图式21. 铁催化TsSeCF3对氮杂环直接三氟甲硒基化反应

Scheme 21. Iron-catalyzed direct trifluoromethylselenylation of nitrogen heterocycles by TsSeCF3

图式22. TsSeCF3参与的苯呋喃的三氟甲硒基化反应

Scheme 22. Trifluoromethylselenylation of benzofuran involved by TsSeCF3

图式23. 钯催化基于C—H活性策略的芳香三氟甲硒基化反应

Scheme 23. Palladium-catalyzed aromatic trifluoromethylselenylation based on a C—H active strategy

图式24. 无过渡金属催化的(杂)芳烃C—H键三氟甲硒基化反应

Scheme 24. Transition-metal-free C—H bond trifluoromethylselenylation of (hetero)arenes

图式25. 无过渡金属催化的三氟甲硒基内酯的合成

Scheme 25. Synthesis of trifluoromethylselenolide without transition metal catalysis

图式26. 无过渡金属催化的杂环三氟甲硒基化合物的合成

Scheme 26. Synthesis of heterocyclic trifluoromethylselenyl compounds without transition metal catalysis

图式27. 炔基铜(I)的三氟甲硒基化反应

Scheme 27. Trifluoromethylselenylation of alkynyl copper(I)

图式28. 烯烃亲电三氟甲硒基化反应

Scheme 28. Electrophilic trifluoromethylselenylation of alkenes

图式29. 羰基化合物直接α-C—H三氟甲硒基化反应

Scheme 29. Direct α-C—H trifluoromethylselenylation of carbonyl compounds

图式30. 羰基化合物的α位三氟甲硒基化反应

Scheme 30. α-Trifluoromethylselenylation of carbonyl compounds

图式31. 富电子(杂)芳烃无金属氧化三氟甲硒基化反应

Scheme 31. Electron-rich (hetero)arene metal-free oxidative trifluoromethylselenylation

图式32. 1,3-二羰基化合物氧化三氟甲硒基化反应

Scheme 32. Oxidative trifluoromethylselenylation of 1,3- dicarbonyl compounds

图式33. N-酰三氟甲硒基吲哚类化合物的合成

Scheme 33. Synthesis of N-acyltrifluoromethylselenoindoles

图式34. 铜介导的多米诺反应合成双三氟甲硒基吲哚衍生物

Scheme 34. Synthesis of bistrifluoromethylselenoindole derivatives by copper-mediated domino reaction

图式35. 铜介导的多米诺反应合成单三氟甲硒基吲哚衍生物

Scheme 35. Synthesis of monotrifluoromethylselenoindole derivatives by copper-mediated domino reaction

图式36. 可见光介导的无金属催化的芳烃三氟甲硒基化反应

Scheme 36. Visible-light-mediated metal-free catalyzed trifluoromethylselenylation of aromatic hydrocarbons

图式37. 双环[1,1,1]戊烷和三氟甲硒基芳基砜的双官能团化反应

Scheme 37. Difunctionalization of bicyclo[1,1,1]pentane and trifluoromethylselenylaryl sulfone

图式38. 无金属光氧化还原催化的未活性烯烃三氟甲硒基化反应

Scheme 38. Metal-free photoredox-catalyzed trifluoromethylselenylation of inactive olefins

图式39. 光氧化还原催化脱羧三氟甲硒基化反应

Scheme 39. Photoredox catalytic decarboxylation trifluoromethylselenylation

图式40. 光催化环烷醇开环三氟甲硒基化反应

Scheme 40. Photocatalytic ring-opening trifluoromethylselenylation of cycloalkanols

图式41. 可见光促进的邻羟基芳烯胺酮的三氟甲硒基化反应

Scheme 41. Visible-light-promoted trifluoromethylselenylation of o-hydroxyarenaminones

图式42. 光氧化还原脱羧三氟甲硒基化反应

Scheme 42. Photoredox decarboxylation trifluoromethylselenylation

图式43. 光氧化还原杂芳烃三氟甲硒基化反应

Scheme 43. Photoredox heteroarene trifluoromethylselenylation

图式44. 光催化芳基锍盐的三氟甲硒基化反应

Scheme 44. Photocatalytic trifluoromethylselenylation of aryl sulfonium salts

参考文献 70

[1]	(a) Zhang, P. B.; Li, W. W.; Qu, W. L.; Shu, Z. G.; Tao, Y. J.; Lin, J. M; Gao, X. Org. Lett. 2021, 23, 9267. doi: 10.1021/acs.orglett.1c03608
	(b) Hu, Z. M.; Ren, J.; Chen, Z. Z.; Yin, S. Y; Wu, F. H.; Liu, C.; Wu, Z.; Wu, J. J. ChemistrySelect 2021, 6, 12276. doi: 10.1002/slct.202102936
	(c) Hu, X. S.; Yu, J. S.; Zhou, J. Chem. Commun. 2019, 55, 13638. doi: 10.1039/C9CC07677H
	(d) Pan, J.; Wu, J. J.; Wu, F. H. Chin. J. Org. Chem. 2020, 41, 983. (in Chinese) doi: 10.6023/cjoc202007025
	(潘军, 吴晶晶, 吴范宏, 有机化学, 2020, 41, 983.)
[2]	Torres, M. E. S.; Morales, A. R.; Peralta, A. S.; Kroneck, P. M. H. Met. Ions Life Sci. 2020, 20, 19.
[3]	(a) Zhang, K.; Xu, X. H.; Qing, F,L. Chin. J. Org. Chem. 2015, 35, 556. (in Chinese) doi: 10.6023/cjoc201501017
	(张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.) doi: 10.6023/cjoc201501017
	(b) Ghosh, K. G.; Das, D.; Garai, S.; Chandu, P.; Sureshkumar, D. J. Org. Chem. 2022.
	(c) Ren, Y. M.; Yan, Q. Q.; Li, Y.; Gao, Y. G.; Zhao, J. C.; Li, L. J.; Liu, Z. Q.; Li, Z. J. J. Org. Chem. 2022.
	(d) Yang, W. C.; Zhang, M. M.; Sun, Y.; Chen, C. Y.; Wang, L. Org. Lett. 2021, 23, 6691. doi: 10.1021/acs.orglett.1c02260
	(e) Zhu, D.; Ding, T. M.; Luo, H. Y.; Ke, H.; Chen, Z. M. Org. Lett. 2020, 22, 7699. doi: 10.1021/acs.orglett.0c02875
[4]	Yang, X. H.; Chang, D. H.; Zhao, R.; Shi, L. Asian J. Org. Chem. 2020, 10, 61. doi: 10.1002/ajoc.202000575
[5]	Aufiero, M.; Sperger, T.; Tsang, A. S.; Schoenebeck, F. Angew. Chem., Int. Ed. 2015, 54, 10322. doi: 10.1002/anie.201503388
[6]	Block, E.; Booker, S. J.; Flores-Penalba, S.; George, G. N.; Gundala, S.; Landgraf, B. J.; Liu, J.; Lodge, S. N.; Pushie, M. J.; Rozovsky, S.; Vattek-katte, A.; Yaghi, R.; Zeng, H. W. ChemBioChem 2016, 17, 1738. doi: 10.1002/cbic.201600266 pmid: 27383291
[7]	Huang, X.; Liu, X.; Luo, Q.; Liu, J.; Shen, J. Chem. Soc. Rev. 2011, 40, 1171. doi: 10.1039/c0cs00046a pmid: 21125082
[8]	Li, S.; Cao, Y.; Jiang, L. Q. Chin. J. Org. Chem. 2022, 42, 434. (in Chinese) doi: 10.6023/cjoc202108001
	(李珊, 曹原, 蒋绿齐, 有机化学, 2022, 42, 434.) doi: 10.6023/cjoc202108001
[9]	Tyrra, W.; Naumann, D.; Hoge, B.; Yagupolskill, Y. L. J. Fluorine Chem. 2003, 119, 101 doi: 10.1016/S0022-1139(02)00276-2
[10]	Han, J. B.; Dong, T.; Vicic, D. A.; Zhang, C. P. Org. Lett. 2017, 19, 3919. doi: 10.1021/acs.orglett.7b01839
[11]	Dong, T.; He, J.; Li, Z. H.; Zhang, C. P. ACS Sustainable Chem. Eng. 2017, 6, 1327. doi: 10.1021/acssuschemeng.7b03673
[12]	Chen, C. H; Hou, C. Q; Wang, Y. G; Hor, T. S.; Weng, Z. Q. Org. Lett. 2014, 16, 524. doi: 10.1021/ol403406y
[13]	Durr, A. B.; Fisher, H. C.; Kalvet, I.; Truong, K. N.; Schoenebeck, F. Angew. Chem., Int. Ed. 2017, 56, 13431. doi: 10.1002/anie.201706423
[14]	Wu, S.; Jiang, T. H.; Zhang, C. P. Org. Lett. 2020, 22, 6016. doi: 10.1021/acs.orglett.0c02109
[15]	(a) Zhao, H. P.; Liang, G. C.; Nie, S. M.; Lu, X. Q.; Pan, C. X.; Zhong, X. X.; Su, G. F.; Mo, D. L. Green Chem. 2020, 22, 404. doi: 10.1039/C9GC03345A
	(b) Ma, X. P.; Nong, C. M.; Zhao, J.; Lu, X. Q; Liang, C.; Mo, D. L. Adv. Synth. Catal. 2019, 362, 478. doi: 10.1002/adsc.201901206
	(c) Zhang, Y. L.; Briski, J.; Zhang, Y.; Rendy, R.; Klumpp, D. A. Org. Lett. 2005, 7, 2505. doi: 10.1021/ol050900q
[16]	Shi, J.; Zhang, C. P. Molecules 2020, 25, 4535. doi: 10.3390/molecules25194535
[17]	Jia, X. Q.; Zhang, Z. Y; Gevorgyan, V. ACS Catal. 2021, 11, 13217. doi: 10.1021/acscatal.1c04183
[18]	Yu, J.; Yang, N. Y.; Cheng, J. T.; Zhan, T. Y.; Luan, C.; Ye, L.; Gu, Q. S.; Li, Z. L.; Chen, G. Q.; Liu, X. Y. Org. Lett. 2021, 23, 1945. doi: 10.1021/acs.orglett.1c00436
[19]	Mudshinge, S. R.; Yang, Y. H.; Xu, B.; Hammond, G. B.; Lu, Z. C. Angew. Chem., Int. Ed. 2022, 61, e202115687.
[20]	(a) Zhang, M. J.; Weng, Z. Q. Adv. Synth. Catal. 2016, 358, 386. doi: 10.1002/adsc.201500575
	(b) Lin, Q. F; Chen, L.; Huang, Y. G.; Rong, M. G.; Yuan, Y. F.; Weng, Z. Q. Org. Biomol. Chem. 2014, 12, 5500. doi: 10.1039/c4ob00403e
[21]	Yang, Y.; Lin, X.; Zheng, Z. W.; Lin, G. L.; Zhang, Y. X; You, Y.; Weng, Z. Q. J. Fluorine Chem. 2017, 204, 1. doi: 10.1016/j.jfluchem.2017.10.001
[22]	Ma, J. A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975. doi: 10.1016/j.jfluchem.2007.04.026
[23]	Zhang, Y. X.; Yang, D. Y.; Weng, Z. Q. Tetrahedron 2017, 73, 3853. doi: 10.1016/j.tet.2017.05.051
[24]	Goel, A.; Ram, V. J. Tetrahedron 2009, 65, 7865. doi: 10.1016/j.tet.2009.06.031
[25]	Zhang, B. S.; Gao, L. Y.; Zhang, Z.; Wen, Y. H.; Liang, Y. M. Chem. Commun. 2018, 54, 1185. doi: 10.1039/C7CC09083H
[26]	Li, Z. B.; Wang, S.; Huo, Y. M; Wang, B.; Yan, J.; Guo, Q. P. Org. Chem. Front. 2021, 8, 3076. doi: 10.1039/D1QO00126D
[27]	Chen, T. T.; You, Y.; Weng, Z. Q. J. Fluorine Chem. 2018, 216, 43. doi: 10.1016/j.jfluchem.2018.10.002
[28]	(a) Naik, R.; Harmalkar, D. S.; Xu, X. Z.; Jang, K.; Lee, K. Eur. J. Med. Chem. 2015, 90, 379. doi: 10.1016/j.ejmech.2014.11.047
	(b) Xu, Z.; Zhao, S. J.; Lv, Z. S.; Feng, L. S.; Wang, Y. L.; Zhang, F.; Bai, L. Y; Deng, J. L. Eur. J. Med. Chem. 2019, 162, 266. doi: 10.1016/j.ejmech.2018.11.025
[29]	Zhang, M. J.; Weng, Z. Q. Org. Lett. 2019, 21, 5838. doi: 10.1021/acs.orglett.9b01922
[30]	Glenadel, Q.; Ghiazza, C.; Tlili, A.; Billard, T. Adv. Synth. Catal. 2017, 359, 3414. doi: 10.1002/adsc.201700904
[31]	Ghiazza, C.; Kataria, A.; Tlili, A.; Toulgoat, F.; Billard, T. Asian J. Org. Chem. 2019, 8, 675. doi: 10.1002/ajoc.201900027
[32]	Grollier, K.; Taponard, A.; De Zordo-Banliat, A.; Magnier, E.; Billard, T. Beilstein J. Org. Chem. 2020, 16, 3032. doi: 10.3762/bjoc.16.252 pmid: 33363671
[33]	Grollier, K.; Chefdeville, E.; De Zordo-Banliat, A.; Pegot, B.; Dagousset, G.; Magnier, E.; Billard, T. Tetrahedron 2021, 100.
[34]	Grollier, K.; Ghiazza, C.; Tlili, A.; Billard, T.; Médebielle, M.; Vantourout, J. C. Eur. J. Org. Chem. 2022, 2022.
[35]	Modak, A.; Pinter, E. N.; Cook, S. P. J. Am. Chem. Soc. 2019, 141, 18405. doi: 10.1021/jacs.9b10316
[36]	Dix, S.; Jakob, M.; Hopkinson, M. N. Chemistry 2019, 25, 7635.
[37]	Glenadel, Q.; Ghiazza, C.; Tlili, A.; Billard, T. Adv. Synth. Catal. 2017, 359, 3414. doi: 10.1002/adsc.201700904
[38]	Ghiazza, C.; Tlili, A.; Billard, T. Molecules 2017, 22, 833. doi: 10.3390/molecules22050833
[39]	Ghiazza, C.; Tlili, A.; Billard, T. Beilstein J. Org. Chem. 2017, 13, 2626. doi: 10.3762/bjoc.13.260
[40]	Zhao, X.; Wei, X. F.; Tian, M. M.; Zheng, X. C.; Ji, L. S.; Li, Q.; Lin, Y. H.; Lu, K. Tetrahedron Lett. 2019, 60, 1796. doi: 10.1016/j.tetlet.2019.06.002
[41]	Liu, J. Y.; Tian, M. M.; Li, A. K.; Ji, L. S.; Qiu, D.; Zhao, X. Tetrahedron Lett. 2021, 66.
[42]	(a) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960. doi: 10.1002/anie.201201666 pmid: 21391562
	(b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. doi: 10.1021/cr900184e pmid: 21391562
	(c) Ackermann, L. Chem. Rev. 2011, 111, 1315. doi: 10.1021/cr100412j pmid: 21391562
[43]	Grollier, K.; Chefdeville, E.; Jeanneau, E.; Billard, T. Chem.-Eur. J. 2021, 27, 12910. doi: 10.1002/chem.202102121
[44]	Li, Y.; Wang, Y.; Ye, Z. G.; Zhang, S. B.; Ye, X. D.; Yuan, Z. L. Org. Lett. 2022, 24, 3009. doi: 10.1021/acs.orglett.2c00916
[45]	Wang, D.; Carlton, C. G.; Tayu, M.; McDouall, J. J. W.; Perry, G. J. P.; Procter, D. J. Angew. Chem., Int. Ed. 2020, 59, 15918. doi: 10.1002/anie.202005531
[46]	Shi, H. F.; Wang, X. Z.; Li, X. X.; Zhang, B. B.; Li, X. M.; Zhang, J. R.; Yang, J. Y.; Du, Y. F. Org. Lett. 2022, 24, 2214.
[47]	Glenadel, Q.; Ismalaj, E.; Billard, T. Org. Lett. 2018, 20, 56. doi: 10.1021/acs.orglett.7b03338 pmid: 29235351
[48]	Ghiazza, C.; Billard, T.; Tlili, A. Chem.-Eur. J. 2017, 23, 10013. doi: 10.1002/chem.201702028
[49]	Ghiazza, C.; Glenadel, Q.; Tlili, A.; Billard, T. Eur. J. Org. Chem. 2017, 2017, 3812. doi: 10.1002/ejoc.201700643
[50]	Ghiazza, C.; Tlili, A.; Billard, T. Eur. J. Org. Chem. 2018, 2018, 3680. doi: 10.1002/ejoc.201800237
[51]	Massolo, E.; Pirola, M.; Rossi, S.; Benincori, T. Molecules 2019, 24, 726. doi: 10.3390/molecules24040726
[52]	Han, Q. Y.; Zhao, C. L.; Dong, T.; Shi, J.; Tan, K. L.; Zhang, C. P. Org. Chem. Front. 2019, 6, 2732. doi: 10.1039/C9QO00631A
[53]	Tan, K. L.; Dong, T.; Zhang, X. Q.; Zhang, C. P. Org. Biomol. Chem. 2020, 18, 1769. doi: 10.1039/D0OB00108B
[54]	Tan, K. L.; Wang, H. N.; Dong, T.; Zhang, C. P. Org. Biomol. Chem. 2021, 19, 5368. doi: 10.1039/D1OB00842K
[55]	Wang, H.; Yao, Y. F.; Zhang, Z. P.; Huang, Y. J.; Weng, Z. Q. J. Org. Chem. 2022, 87, 3605. doi: 10.1021/acs.joc.1c03156
[56]	Wang, H.; Yao, Y. F.; You, Y.; Huang, Y. J.; Weng, Z. Q. Org. Biomol. Chem. 2022, 20, 2115. doi: 10.1039/D2OB00063F
[57]	(a) Chan, A. Y.; Perry, I. B.; Bissonnette, N. B.; Buksh, B. F.; Edwards, G. A.; Frye, L. I.; Garry, O. L.; Lavagnino, M. N.; Li, B. X.; Liang, Y.; Mao, E.; Millet, A.; Oakley, J. V.; Reed, N. L.; Sakai, H. A.; Seath, C. P.; MacMillan, D. W. C. Chem. Rev. 2022, 122, 1485. doi: 10.1021/acs.chemrev.1c00383
	(b) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Soc. Rev. 2016, 45, 2044. doi: 10.1039/C5CS00655D
	(c) Cheng, W. M.; Shang, R. ACS Catal. 2020, 10, 9170. doi: 10.1021/acscatal.0c01979
[58]	Ghiazza, C.; Debrauwer, V.; Monnereau, C.; Khrouz, L.; Medebielle, M.; Billard, T.; Tlili, A. Angew. Chem., Int. Ed. 2018, 57, 11781. doi: 10.1002/anie.201806165
[59]	Ghiazza, C.; Monnereau, C.; Khrouz, L.; Médebielle, M.; Billard, T.; Tlili, A. Synlett 2018, 30, 777. doi: 10.1055/s-0037-1610347
[60]	(a) Pätzel, M.; Sanktjohanser, M.; Doss, A.; Henklein, P.; Szeimies, G. Eur. J. Org. Chem. 2004, 2004, 493. doi: 10.1002/ejoc.200300554 pmid: 17203493
	(b) de Meijere, A.; Zhao, L.; Belov, V. N.; Bossi, M.; Noltemeyer, M.; Hell, S. W. Chem.-Eur. J. 2007, 13, 2503. pmid: 17203493
	(c) Westphal, M. V.; Wolfstadter, B. T.; Plancher, J. M.; Gatfield, J.; Carreira, E. M. ChemMedChem 2015, 10, 461. doi: 10.1002/cmdc.201402502 pmid: 17203493
	(d) Goh, Y. L.; Cui, Y. T.; Pendharkar, V.; Adsool, V. A. ACS Med. Chem. Lett. 2017, 8, 616. pmid: 17203493
[61]	Wu, Z.; Xu, Y. H.; Liu, J.; Wu, X. X.; Zhu, C. Sci. China Chem. 2020, 63, 1025. doi: 10.1007/s11426-020-9733-y
[62]	Lei, Y. J.; Yang, J.; Wang, Y. W.; Wang, H. Y.; Zhan, Y.; Jiang, X. X.; Xu, Z. Q. Green Chem. 2020, 22, 4878. doi: 10.1039/C9GC03936H
[63]	Grollier, K.; De Zordo-Banliat, A.; Bourdreux, F.; Pegot, B.; Dagousset, G.; Magnier, E.; Billard, T. Chem.-Eur. J. 2021, 27, 6028. doi: 10.1002/chem.202100053 pmid: 33538377
[64]	Zhang, Q. Y.; Yuan, W. Q.; Shi, Y. B.; Pan, F. Tetrahedron Lett. 2022, 98.
[65]	Lu, L. H.; Zhao, X. J.; Dessie, W.; Xia, X. W.; Duan, X. J.; He, J.; Wang, R.; Liu, Y.; Wu, C. Org. Biomol. Chem. 2022, 20, 1754. doi: 10.1039/D1OB02402G
[66]	Han, Q. Y.; Tan, K. L.; Wang, H. N.; Zhang, C. P. Org. Lett. 2019, 21, 10013. doi: 10.1021/acs.orglett.9b03941
[67]	De Zordo-Banliat, A.; Barthélémy, L.; Bourdreux, F.; Tuccio, B.; Dagousset, G.; Pégot, B.; Magnier, E. Eur. J. Org. Chem. 2020, 2020, 506
[68]	(a) Kaiser, D.; Klose, I.; Oost, R.; Neuhaus, J.; Maulide, N. Chem. Rev. 2019, 119, 8701. doi: 10.1021/acs.chemrev.9b00111 pmid: 32742188
	(b) Fan, R.; Tan, C.; Liu, Y.; Wei, Y. G.; Zhao, X. W.; Liu, X. Y.; Tan, J. J; Yoshida, H. Chin. Chem. Lett. 2021, 32, 299. doi: 10.1016/j.cclet.2020.06.003 pmid: 32742188
	(c) Kozhushkov, S. I.; Alcarazo, M. Eur. J. Inorg. Chem. 2020, 2020, 2486. doi: 10.1002/ejic.202000249 pmid: 32742188
	(d) Tian, Z. Y.; Hu, Y. T.; Teng, H. B.; Zhang, C. P. Tetrahedron Lett. 2018, 59, 299. doi: 10.1016/j.tetlet.2017.12.005 pmid: 32742188
[69]	Tian, Z. Y.; Zhang, C. P. Org. Chem. Front. 2022, 9, 2220. doi: 10.1039/D2QO00235C
[70]	Sperger, T.; Guven, S.; Schoenebeck, F. Angew. Chem., Int. Ed. 2018, 57, 16903. doi: 10.1002/anie.201810950