芳基二硫醚作为自由基硫试剂构建C—S键研究进展

doi:10.6023/cjoc202305005

摘要/Abstract

含硫化合物在医药、农业、天然产物和有机材料等方面有广泛的应用, 因而引起了科研人员极大的兴趣, 开发高效、绿色的含硫化合物的构建和转化方法具有重要意义. 近年来, 稳定、低毒的芳基二硫醚类化合物作为刺激性强、毒性大的硫醇类化合物的理想替代物, 为各种含硫化合物的构建开辟了一条新的途径. 从光催化、非金属参与和过渡金属催化三个方面分类综述了芳基二硫醚作为自由基硫试剂构建C—S键的研究进展.

关键词: 芳基二硫醚, C—S键的构建, 自由基, 绿色合成

Sulfur-containing compounds have been widely applied in numerous natural products, pharmaceuticals, agrochemicals, and organic functional materials, which has attracted great interest among researchers. Therefore, it is of great significance to develop efficient and green methods for the construction and transformation of sulfur-containing compounds. In recent years, stable and low-toxicity aryl disulfides have been used as ideal substitutes for thiol compounds endured with strong irritation and toxicity, which has opened up a new path for the construction of various sulfur-containing compounds. In this paper, the research progress of aryl disulfides as radical sulfur reagents to build C—S bond is reviewed, which is divided into three parts: photocatalysis, non-metallic participation, and transition metal catalysis.

Key words: aryl disulfides, C—S bond formation, radical, green-synthesis

引用此文

程飞, 孙琪雯, 卢江溶, 王兴兰, 张吉泉. 芳基二硫醚作为自由基硫试剂构建C—S键研究进展[J]. 有机化学, 2023, 43(11): 3728-3744.

Fei Cheng, Qiwen Sun, Jiangrong Lu, Xinglan Wang, Jiquan Zhang. Research Progress on the Construction of C—S Bond Using Aryl Disulfides as Radical Sulfur Reagents[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3728-3744.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 32

图式1. 醚α-C(sp3)—H直接硫化

Scheme 1. Direct sulfenylation at α-C(sp3)—H of ethers

图式2. 硫化吲哚衍生物的合成

Scheme 2. Synthesis of thio-indole derivatives

图式3. 硫代苯并呋喃衍生物的合成

Scheme 3. Synthesis of thio-benzofuran derivatives

图式4. 苯乙烯的β-羟基硫化和β-烷氧硫化

Scheme 4. β-Hydroxysulfurization and β-alkoxysulfurization of styrenes

图式5. 炔基硫醚的合成

Scheme 5. Synthesis of alkyne sulfides

图式6. 吲哚C-3位硫化

Scheme 6. C-3 sulfenylation of indoles

图式7. 吲哚C(sp2)—H直接硫化

Scheme 7. Direct thiolation at indole C(sp2)—H

图式8. 烯丙基C(sp3)—H直接硫化

Scheme 8. Direct thiolation at allylic C(sp3)—H

图式9. 环丁酮肟酯硫化

Scheme 9. Thiolation of cycloketone oxime esters

图式10. 富电子卤代杂芳烃的甲基硫化

Scheme 10. Methylthiolation of halogenated electron-rich heteroarenes

图式11. 光催化芳基肼自由基硫化

Scheme 11. Photocatalyzed arylhydrazine radical sulfenylation

图式12. 4-硫代3,3-二氟-γ-内酰胺的合成

Scheme 12. Synthesis of 4-thio-substituted 3,3-difluoro-γ-lactams

图式13. 甲苯及其衍生物的C(sp3)—H键活化硫醚化

Scheme 13. Thioetherification of toluene and its derivatives at C(sp3)—H

图式14. 叔丁基过氧化物直接氧化C(sp3)—H合成烷基芳基硫醚

Scheme 14. Synthesis of alkyl aryl thioethers through tert-butyl peroxide directly oxidative C(sp3)—H

图式15. 醛的C(sp2)—H氧化合成硫酯

Scheme 15. Syntheses of thiol esters by oxidative aldehydes at C(sp2)―H

图式16. 芳基甲基硫化物的合成

Scheme 16. Synthsis of aryl methyl sulfides

图式17. 磺酰化氧化吲哚的合成

Scheme 17. Synthesis of sulfone-containing oxindoles

图式18. 烷基芳基硫化物的合成

Scheme 18. Synthesis of alkyl aryl sulfides

图式19. N-取代吡唑酮直接C—H硫化

Scheme 19. Direct C—H thiolation of N-substituted pyrazo- lones

图式20. 硫化异喹啉酮衍生物的合成

Scheme 20. Synthesis of thio-substituted isoquinolinones

图式21. 铁介导烷基芳基硫醚的合成

Scheme 21. Iron-mediated synthesis of alkyl aryl sulfides

图式22. 铁催化环烷基过氧化物硫化

Scheme 22. Iron-catalyzed thiolation of cycloalkyl hydroperoxides

图式23. 硅基过氧化物导向的C(sp3)—H硫醚化反应

Scheme 23. Peroxide-directed C(sp3)—H thioetherification by resident silylperoxides

图式24. 铁催化硫代γ-内酯合成

Scheme 24. Iron-catalyzed synthesis of sulfurated γ-lactones

图式25. 钴催化硫代氧化吲哚的合成

Scheme 25. Cobalt-catalyzed synthesis of sulfurated oxindoles

图式26. 镍催化C(sp2)—H键的硫化

Scheme 26. Ni-catalyzed thiolation of C(sp2)—H bonds

图式27. 镍催化苯胺衍生物C(sp2)—H的硫化

Scheme 27. Ni-catalyzed thiolation of aniline derivatives at C(sp2)—H

图式28. 氧化还原活性酯的脱羧硫化

Scheme 28. Decarboxylative thiolation of RAE

图式29. 银/铜共催化富电子芳烃直接硫化

Scheme 29. Silver/copper-cocatalyzed direct sulfenylation of rich arenes

图式30. 铜催化二茂铁酰胺的硫化

Scheme 30. Copper-catalyzed thiolation of ferroceneamide

图式31. 铜催化远端C—H活化合成5-硫代8-酰胺喹啉

Scheme 31. Copper-mediated remote C—H bond thiolation of 8-aminoquinolines on the C5 position

图式32. 铜催化芳香胺对位选择性硫化

Scheme 32. Copper-catalyzed the para-selective thiolation of aromatic amines

参考文献 63

[1]	(a) Wang, N.; Saidhareddy, P.; Jiang, X. Nat. Prod. Rep. 2020, 37, 246. doi: 10.1039/C8NP00093J
	(b) Feng, M.; Tang, B.; Liang, S.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200. doi: 10.2174/1568026615666150915111741
	(c) Scot, K. A.; Njardarson, J. T. Top. Curr. Chem. 2018, 376, 5.
	(d) Wang, Q.; Guan, J.; Wan, J.; Li, Z. RSC Adv. 2020, 10, 24397. doi: 10.1039/D0RA04155F
	(e) Xu, W. M.; Han, F. F.; He, M.; Hu, D. Y.; He, J.; Yang, S.; Song, B. A. J. Agric. Food Chem. 2012, 60, 1036. doi: 10.1021/jf203772d
	(f) Devendar, P.; Yang, G.-F. Top. Curr. Chem. 2017, 375, 82.
	(g) Cinar, M. E.; Ozturk, T. Chem. Rev. 2015, 115, 3036. doi: 10.1021/cr500271a
	(h) Turkoglu, G.; Cinar, M. E.; Ozturk, T. Top. Curr. Chem. 2017, 375, 84.
[2]	(a) Dong, B.; Shen, J.; Xie, L.-G. Org. Chem. Front. 2023, 10, 1322. doi: 10.1039/D2QO01699K
	(b) Huang, S.; Wang, M.; Jiang, X. Chem. Soc. Rev. 2022, 51, 8351. doi: 10.1039/D2CS00553K
	(c) Chen, Z.-W.; Bai, R.; Annamalai, P.; Badsara, S. S.; Lee, C.-F. New J. Chem. 2022, 46, 15. doi: 10.1039/D1NJ04662D
	(d) Gan, Z.; Zhu, X.; Yan, Q.; Song, X.; Yang, D. Chin. Chem. Lett. 2021, 32, 1705. doi: 10.1016/j.cclet.2020.12.046
	(e) Sun, K.; Lv, Y.; Shi, Z.; Fu, F.; Zhang, C.; Zhang, Z. Sci. China Chem. 2017, 60, 730. doi: 10.1007/s11426-016-0412-0
[3]	Chauhan, P.; Mahajan, S.; Enders, D. Chem. Rev. 2014, 114, 8807. doi: 10.1021/cr500235v pmid: 25144663
[4]	(a) Glass, R. S. Top. Curr. Chem. 2018, 376, 22.
	(b) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048. doi: 10.1039/C8QO01353E
	(c) Wei, Y.-F.; Gao, W.-C.; Chang, H.-H.; Jiang, X. Org. Chem. Front. 2022, 9, 6684. doi: 10.1039/D2QO01447E
[5]	(a) Batista, G. M. F.; de Castro, P. P.; dos Santos, J. A.; Skrydstrup, T.; Amarante, G. W. Org. Chem. Front. 2021, 8, 326. doi: 10.1039/D0QO01226B
	(b) Wu, R.; Huang, K.; Qiu, G.; Liu, J.-B. Synthesis 2019, 51, 3567. doi: 10.1055/s-0039-1690015
[6]	(a) Yi, H.; Zhang, G.-T.; Wang, H.-M.; Huang, Z.-Y.; Wang, J.; Singh, A. K.; Lei, A.-W. Chem. Rev. 2017, 117, 9016. doi: 10.1021/acs.chemrev.6b00620
	(b) Liu, C.; Liu, D.; Lei, A.-W. Acc. Chem. Res. 2014, 47, 3459. doi: 10.1021/ar5002044
	(c) Xu, P.; Li, W.-P.; Xie, J.; Zhu, C.-J. Acc. Chem. Res. 2018, 51, 484. doi: 10.1021/acs.accounts.7b00565
	(d) Bhunia, A.; Studer, A. Chem, 2021, 7, 2060. doi: 10.1016/j.chempr.2021.03.023
[7]	(a) Zhao, X.; Ou, Y.-C.; Liu, Y.; Maruoka, K. J.; Chen, Q. Chin. J. Org. Chem. 2021, 41, 3366. (in Chinese) doi: 10.6023/cjoc202105015 pmid: 35520400
	(赵喜, 区颖聪, 刘艳, Keiji, Maruoka, 陈迁, 有机化学, 2021, 41, 3366.) doi: 10.6023/cjoc202105015 pmid: 35520400
	(b) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048. doi: 10.1039/C8QO01353E pmid: 35520400
	(c) Srivastava, V.; Singh, P. K.; Srivastava, A.; Singh, P. P. RSC. Adv. 2020, 10, 20046. doi: 10.1039/d0ra03086d pmid: 35520400
	(d) Yang, W.; Zhang, M.; Chen, W.; Yang, X.; Feng, J. Chin. J. Org. Chem. 2020, 40, 4060. (in Chinese) doi: 10.6023/cjoc202005039 pmid: 35520400
	(杨文超, 张明明, 陈旺, 杨小虎, 冯建国, 有机化学, 2020, 40, 4060.) doi: 10.6023/cjoc202005039 pmid: 35520400
	(e) Corce, V.; Ollivier, C.; Fensterbank, L. Chem. Soc. Rev. 2022, 51, 1470. doi: 10.1039/D1CS01084K pmid: 35520400
	(f) Wang, X.; Meng, J.; Zhao, D.; Tang, S.; Sun, K. Chin. Chem. Lett. 2023, 34, 107736. doi: 10.1016/j.cclet.2022.08.016 pmid: 35520400
[8]	Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77. doi: 10.1126/science.1161976 pmid: 18772399
[9]	(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r pmid: 30854847
	(b) Gui, Y.-Y.; Sun, L.; Lu, Z.-P.; Yu, D.-G. Org. Chem. Front. 2016, 3, 522. doi: 10.1039/C5QO00437C pmid: 30854847
	(c) Chen, J.-R.; Hu, X.-Q.; Lua, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 204. pmid: 30854847
	(d) Chen, J.-R. Hu, X.-Q. Lu, L.-Q.; Xiao, W.-J. Acc. Chem. Res. 2016, 49, 1911. doi: 10.1021/acs.accounts.6b00254 pmid: 30854847
	(e) Chen, J.-R.; Yan, D.-M.; Wei, Q.; Xiao, W.-J. ChemPhotoChem 2017, 1, 148. doi: 10.1002/cptc.v1.5 pmid: 30854847
	(f) Troian-Gautier, L.; Turlington, M. D.; Wehlin, S. A. M.; Maurer, A. B.; Brady, M. D.; Swords, W. B.; Meyer, G. J. Chem. Rev. 2019, 119, 4628. doi: 10.1021/acs.chemrev.8b00732 pmid: 30854847
	(g) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. doi: 10.1021/acs.chemrev.0c00030 pmid: 30854847
[10]	Li, J.; Zhang, J.; Tan, H.; Wang, D.-Z. Org. Lett. 2015, 17, 2522. doi: 10.1021/acs.orglett.5b01053
[11]	Zhu, X.; Xie, X.; Li, P.; Guo, J.; Wang, L. Org. Lett. 2016, 18, 1546. doi: 10.1021/acs.orglett.6b00304
[12]	Shi, Q.; Li, P.; Zhang, Y.; Wang, L. Org. Chem. Front. 2017, 4, 1322. doi: 10.1039/C7QO00152E
[13]	Li, X.-Z.; Xu, Z.-L.; Wang, L.; Wang, F.; Yang, J.-G.; Li, P. H. ChemPhotoChem 2021, 5, 142. doi: 10.1002/cptc.v5.2
[14]	Ruan, H.; Meng, L.-G.; Zhu, L.; Wang, L. Adv. Synth. Catal. 2019, 361, 3217. doi: 10.1002/adsc.v361.13
[15]	Reddy, M. B.; Anandhan, R. Chem. Commun. 2020, 56, 3781. doi: 10.1039/D0CC00815J
[16]	Ye, R.; Ruan, H.; Xu, H.; Li, Z.; Meng, L.-G.; Wang, L. Org. Chem. Front. 2021, 8, 5345. doi: 10.1039/D1QO01082D
[17]	Ye, L.-M.; Chen, J.; Mao, P.; Zhang, X.-J.; Yan, M. Tetrahedron Lett. 2017, 58, 2743.
[18]	Rathore, V.; Kumar, S. Green. Chem. 2019, 21, 2670. doi: 10.1039/C9GC00007K
[19]	(a) Zhou, R.; Liu, H.; Tao, H.; Yu, X.; Wu, J. Chem. Sci. 2017, 8, 4654. doi: 10.1039/C7SC00953D
	(b) Fan, X.-Z.; Rong, J.-W.; Wu, H.-L.; Zhou, Q.; Deng, H.-P.; Tan, J. D.; Xue, C.-W.; Wu, L.-Z.; Tao, H.-R.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 8514. doi: 10.1002/anie.v57.28
[20]	Kim, J.; Kang, B.; Hong, S. H. ACS Catal. 2020, 10, 6013. doi: 10.1021/acscatal.0c01232
[21]	(a) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055. doi: 10.1021/ja00003a057
	(b) Boivin, J.; Fouquet, E.; Schiano, A.-M.; Zard, S. Z. Tetrahedron 1994, 50, 1769. doi: 10.1016/S0040-4020(01)80851-6
	(c) Boivin, J.; Fouquet, E.; Zard, S. Z. Tetrahedron 1994, 50, 1757. doi: 10.1016/S0040-4020(01)80850-4
[22]	Pratley, C.; Fenner, S.; Murphy, J. A. Chem. Rev. 2022, 122, 8181. doi: 10.1021/acs.chemrev.1c00831 pmid: 35285636
[23]	Nishimura, T.; Yoshinaka, T.; Nishiguchi, Y.; Maeda, Y.; Uemura, S. Org. Lett. 2005, 7, 2425. pmid: 15932214
[24]	Anand, D.; He, Y.; Li, L.; Zhou, L. Org. Biomol. Chem. 2019, 17, 533. doi: 10.1039/C8OB02987C
[25]	Sandfort, F.; Knecht, T.; Pinkert, T.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2020, 142, 6913. doi: 10.1021/jacs.0c01630
[26]	Li, R.; Shi, T.; Chen, X.-L.; Lv, Q.-Y.; Zhang, Y.-L.; Peng, Y.-Y.; Qu, L.-B.; Yu, B. New J. Chem. 2019, 43, 13642. doi: 10.1039/C9NJ03692J
[27]	Ye, Z.-P.; Xia, P.-J.; Liu, F.; Hu, Y.-Z.; Song, D.; Xiao, J.-A.; Huang, P.; Xiang, H.-Y.; Chen, X.-Q.; Yang, H. J. Org. Chem. 2020, 85, 5670. doi: 10.1021/acs.joc.9b03490
[28]	Wang, L.; Liu, X.; Lin, G.; Jin, H.; Jiao, M.; Liu, X.; Luo, S. Chin. J. Org. Chem. 2023, 43, 2848. (in Chinese) doi: 10.6023/cjoc202210018
	(王灵娜, 刘晓庆, 林钢, 金泓颖, 焦民均, 刘雪粉, 罗书平, 有机化学, 2023, 43, 2848.) doi: 10.6023/cjoc202210018
[29]	(a) Hong, J.; Li, M.; Zhang, J.; Sun, B.; Mo, F. ChemSusChem 2019, 12, 6. doi: 10.1002/cssc.v12.1 pmid: 35965690
	(b) Song, S.-Z.; Meng, Y.-N.; Li, Q.; Wei, W.-T. Adv. Synth. Catal. 2020, 362, 2120. doi: 10.1002/adsc.v362.11 pmid: 35965690
	(c) Qiao, J.; Song, Z.-Q.; Huang, C.; Ci, R.-N.; Liu, Z.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Angew. Chem., Int. Ed. 2021, 60, 27201. doi: 10.1002/anie.v60.52 pmid: 35965690
	(d) Lasso, J. D.; Castillo-Pazos, D. J.; Li, C.-J. Chem. Soc. Rev. 2021, 50, 10955. doi: 10.1039/d1cs00380a pmid: 35965690
	(e) Zhang, Y.; Sahoo, P. K.; Ren, P.; Qin, Y.; Cauwenbergh, R.; Nimmegeers, P.; SivaRaman, G.; Van Passel, S.; Guidetti, A.; Das, S. Chem. Commun. 2022, 58, 11454. doi: 10.1039/D2CC02661A pmid: 35965690
	(f) Golden, D. L.; Suh, S.-E.; Stahl, S. S. Nat. Rev. Chem. 2022, 6, 405. doi: 10.1038/s41570-022-00388-4 pmid: 35965690
[30]	Tang, R.-Y.; Xie, Y.-X.; Xie, Y.-L.; Xiang, J.-N.; Li, J.-H. Chem. Commun. 2011, 47, 12867. doi: 10.1039/c1cc15397h
[31]	Guo, S.-R.; Yuan, Y.-Q.; Xiang, J.-N. Org. Lett. 2013, 15, 4654. doi: 10.1021/ol402281f
[32]	Du, B.-N.; Jin, B.; Sun, P.-P. Org. Lett. 2014, 16, 3032. doi: 10.1021/ol5011449
[33]	Zeng, J.-W.; Liu, Y.-C.; Hsieh, P.-A.; Huang, Y.-T.; Yi, C.-L.; Badsara, S. S.; Lee, C.-F. Green Chem. 2014, 16, 2644. doi: 10.1039/C4GC00025K
[34]	He, C.-H.; Qian, X.-W.; Sun, P.-P. Org. Biomol. Chem. 2014, 12, 6072. doi: 10.1039/C4OB01159G
[35]	Wu, X.; Wang, Y. Tetrahedron Lett. 2018, 59, 1240. doi: 10.1016/j.tetlet.2018.02.043
[36]	Zhang, M.-Z.; Ji, P.-Y.; Liu, Y.-F.; Xu, J.-W.; Guo, C.-C. Adv. Synth. Catal. 2016, 358, 2976. doi: 10.1002/adsc.v358.18
[37]	Shahidzadeh, E. S.; Nowrouzi, N.; Abbasi, M. Appl. Organomet. Chem. 2019, 33, e5211. doi: 10.1002/aoc.v33.11
[38]	Kittikool, T.; Yotphan, S. Eur. J. Org. Chem. 2020, 2020, 961. doi: 10.1002/ejoc.v2020.8
[39]	Wang, X.-L.; Bai, X.; Wu, C.-F.; Dong, Y.-X.; Zhang, M.; Fan, L.-L.; Tang, L.; Yang, Y.-Y.; Zhang, J.-Q. Asian J. Org. Chem. 2021, 10, 386. doi: 10.1002/ajoc.v10.2
[40]	(a) Yi, H.; Zhang, G.; Wang, H. M.; Huang, Z. Y.; Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016. doi: 10.1021/acs.chemrev.6b00620
	(b) Korch, K. M.; Watson, D. A. Chem. Rev. 2019, 119, 8192. doi: 10.1021/acs.chemrev.8b00628
[41]	(a) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 7, 13. doi: 10.1246/cl.1978.13
	(b) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Katoand, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385. doi: 10.1246/bcsj.53.1385
[42]	(a) Badsara, S. S.; Cheng, C.-C.; Lee, C.-F. Asian J. Org. Chem. 2014, 3, 1197. doi: 10.1002/ajoc.v3.11 pmid: 33528480
	(b) Sundaravelu, N.; Sangeetha, S.; Sekar, G. Org. Biomol. Chem. 2021, 19, 1459. doi: 10.1039/d0ob02320e pmid: 33528480
	(c) Chen, Z.-W.; Bai, R.; Annamalai, P.; Badsara, S. S.; Lee, C.-F. New J. Chem. 2022, 46, 15. doi: 10.1039/D1NJ04662D pmid: 33528480
	(d) Huang, S.; Wang, M.; Jiang, X. Chem. Soc. Rev. 2022, 51, 8351. doi: 10.1039/D2CS00553K pmid: 33528480
[43]	(a) Bauer, I.; Knölker, H.-J. Chem. Rev. 2015, 115, 3170. doi: 10.1021/cr500425u
	(b) Wei, D.; Darcel, C. Chem. Rev. 2019, 119, 2550. doi: 10.1021/acs.chemrev.8b00372
	(c) Liang, Q.; Song, D. Chem. Soc. Rev. 2020, 49, 1209. doi: 10.1039/C9CS00508K
	(d) Rana, S.; Biswas, J.-P.; Paul, S.; Paik, A.; Maiti, D. Chem. Soc. Rev. 2021, 50, 243. doi: 10.1039/D0CS00688B
[44]	Smaligo, A. J.; Kwon, O. Org. Lett. 2019, 21, 8592. doi: 10.1021/acs.orglett.9b03186 pmid: 31573208
[45]	Sun, Q.-X.; Chen, H.; Liu, S.; Wang, X.-Q.; Duan, X.-H.; Guo, L.-N. J. Org. Chem. 2021, 86, 11987. doi: 10.1021/acs.joc.1c01366
[46]	Groendyke, B. J.; Modak, A.; Cook, S. P. J. Org. Chem. 2019, 84, 13073. doi: 10.1021/acs.joc.9b01979 pmid: 31524395
[47]	(a) Lin, J.; Song, R.-J.; Hu, M.; Li, J.-H. Chem. Rec. 2019, 19, 440. doi: 10.1002/tcr.v19.2-3
	(b) Li, Z.-L.; Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y. Chem. Soc. Rev. 2020, 49, 32. doi: 10.1039/C9CS00681H
	(c) Wang, D.-K.; Li, L.; Xu, Q.; Zhang, J.; Zheng, H.; Wei, W.-T. Org. Chem. Front. 2021, 8, 7037. doi: 10.1039/D1QO01002F
[48]	Cheng, F.; Wang, L.-L.; Mao, Y.-H.; Dong, Y.-X.; Liu, B.; Zhu, G.-F.; Yang, Y.-Y.; Guo, B.; Tang, L.; Zhang, J.-Q. J. Org. Chem. 2021, 86, 8620. doi: 10.1021/acs.joc.1c00284
[49]	Cheng, F.; Bai, X.; Sun, Q.-W.; Zhu, G.-F.; Dong, Y.-X.; Yang, Y.-Y.; Gao, X.-L.; Guo, B.; Tang, L.; Zhang, J.-Q. Org. Biomol. Chem. 2022, 20, 6423. doi: 10.1039/D2OB00877G
[50]	Yang, K.; Wang, Y.-Q.; Chen, X.-Y.; Kadi, A.-A.; Fun, H.-K.; Sun, H.; Zhang, Y.; Lu, H.-J. Chem. Commun. 2015, 51, 3582. doi: 10.1039/C4CC10431E
[51]	Omer, H. M.; Liu, P. J. Am. Chem. Soc. 2017, 139, 9909. doi: 10.1021/jacs.7b03548
[52]	Meller, T.; Ackermann, L. Chem. Eur. J. 2016, 22, 14151. doi: 10.1002/chem.v22.40
[53]	(a) Zhang, Y.; Ma, D.; Zhang, Z. Arabian J. Chem. 2022, 15, 103922. doi: 10.1016/j.arabjc.2022.103922
	(b) Parida, S. K.; Mandal, T.; Das, S.; Hota, S. K.; De Sarkar, S.; Murarka, S. ACS Catal. 2021, 11, 1640. doi: 10.1021/acscatal.0c04756
[54]	Xiao, Z.; Wang, L.; Wei, J.; Ran, C.; Liang, S.; Shang, J.; Chen, G.-Y.; Zheng, C. Chem. Commun. 2020, 56, 4164. doi: 10.1039/D0CC00451K
[55]	Li, Z.; Wang, K. F.; Zhao, X.; Ti, H.-H.; Liu, X.-G.; Wang, H.-G. Nat. Commun. 2020, 11, 5036. doi: 10.1038/s41467-020-18834-6
[56]	Yan, G.; Borah, A. J.; Wang, L. Org. Biomol. Chem. 2014, 12, 9557. doi: 10.1039/C4OB01992J
[57]	Mittal, R. K.; Aggarwal, M.; Purohit, P.; Mittal, R. K.; Aggarwal, M.; Khatana, K.; Purohit, P. Med. Chem. 2023, 19, 31. doi: 10.2174/1573406418666220303151919
[58]	Deb, M.; Singh, J.; Mallik, S.; Hazra, S.; Elias, A. J. New. J. Chem. 2017, 41, 14528. doi: 10.1039/C7NJ02388J
[59]	Sattar, M.; Shareef, M.; Patidar, K.; Kumar, S. J. Org. Chem. 2018, 83, 8241. doi: 10.1021/acs.joc.8b00974 pmid: 29878778
[60]	(a) Sasmal, S.; Dutta, U.; Lahiri, G. K.; Maiti, D. Chem. Lett. 2020, 49, 1406. doi: 10.1246/cl.200500
	(b) Sinha, S. K.; Guin, S.; Maiti, S.; Biswas, J. P.; Porey, S.; Maiti, D. Chem. Rev. 2022, 122, 5682. doi: 10.1021/acs.chemrev.1c00220
[61]	(a) Dodds, A. C.; Sutherland, A. J. Org. Chem. 2021, 86, 5922. doi: 10.1021/acs.joc.1c00448
	(b) Nalbandian, C. J.; Brown, Z. E.; Alvarez, E.; Gustafson, J. L. Org. Lett. 2018, 20, 3211. doi: 10.1021/acs.orglett.8b01066
[62]	Zhu, L.; Qiu, R.; Cao, X.; Xiao, S.; Xu, X.; Au, C.-T.; Yin, S.-F. Org. Lett. 2015, 17, 5528. doi: 10.1021/acs.orglett.5b02511
[63]	Paul, B.; Das, S.; Chatterjee, I. Org. Lett. 2023, 25, 653. doi: 10.1021/acs.orglett.2c04261