Research Progress on Synthesis of Thioflavonoids

doi:10.6023/cjoc202301004

Abstract

Thioflavonoids are the sulfur counterparts of flavonoids, which have a wide range of applications in the fields of medicine, material science, organic synthesis and others. Therefore, it is of great significance to develop efficient synthetic methods to obtain thioflavonoids with diverse structures. The synthetic approaches of thioflavonoids and key steps of reaction mechanisms according to the classification of thioflavonoids are summarized, and the development prospect of this research field is prospected.

Key words: thioflavonoids, heterocycles, asymmetric synthesis, transition-metal catalysis, organocatalysis

Cite this article

Ling Meng, Jun Wang. Research Progress on Synthesis of Thioflavonoids[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 873-891.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 51

Figure 1. Classification of thioflavonoids and bioactive molecules containing benzo thiopyran scaffold

Scheme 1. (a) Trifluoromethanesulfonic acid-catalyzed sequential alkylation/cyclic acylation reaction; (b) proposed mechanis

Scheme 2. (a) Cu-catalyzed domino reaction of 2'-iodochalcones or 2'-bromochalcones; (b) proposed mechanism

Scheme 3. Rhodium-catalyzed alkyne hydroacylation/thio-conjugate addition

Scheme 4. Addition reactions of thiochromones with diarylcuprates

Scheme 5. (a) Cu-catalyzed domino reaction of 2'-iodo/bromochalcones and rongalite; (b) proposed mechanism

Scheme 6. Synthesis of thiochromanones from 2'-nitrochalcones and xanthate

Scheme 7. Rh-catalyzed formal conjugate addition of arylzinc reagents to thiochromones

Scheme 8. Cu-catalyzed formal conjugate addition to thiochromones with alkylmagnesium bromides

Scheme 9. Zn-ProPhenol catalyzed vinylogous addition of butenolides to (thio)chromones

Scheme 10. Cu-catalyzed enantioselective alkynylation of thiochromones

Scheme 11. Plausible mechanism of Cu-catalyzed alkynylation of thiochromones

Scheme 12. Ru-catalyzed asymmetric reduction of 2-aryl(thio)chromones

Scheme 13. Cu-catalyzed asymmetric reduction of (thio)chromones

Scheme 14. Enantioselective catalytic intramolecular Stetter reaction

Scheme 15. Electrophilic addition of α-diazoesters with ketones

Scheme 16. Enantioselective synthesis of tetralones, chromanones, and thiochromanones by organocatalytic enantioselective protonation

Scheme 17. Chiral spiro phosphoric acid-catalyzed Friedel-Crafts conjugate addition/enantioselective protonation reactions

Scheme 18. Pd-catalyzed cyclization for synthesis of thiochromenes

Scheme 19. Cu-catalyzed domino synthesis of thiochromenes

Scheme 20. Coupling reaction of o-bromobenzaldehydes and β-nitrostyrenes with sodium sulfidenonahydrate

Scheme 21. Synthesis of thiochromene derivatives through hydroarylation of propargyl thioethers

Scheme 22. Organocatalyzed tandem enantioselective thio- Michael-aldol reactions

Scheme 23. Catalyst 24-promoted cascade Michael-aldol reactions of α,β-unsaturated aldehydes with 2-mercaptobenzaldehydes

Scheme 24. Organocatalyzed Michael-aldol reaction of 2-mercaptobenzaldehydes with α,β-unsaturated oxazolidinones

Scheme 25. Catalyst 25 promoted domino Michael-aldol reactions of 2-mercaptobenzaldehydes with maleimides

Scheme 26. Catalyst 24 promoted domino thia-Michael/aldol reaction of 2-mercaptoacetophenones and enals

Scheme 27. Enantioselective tandem Michael-Henry reaction of 2-mercaptobenzaldehydes with β-nitrostyrenes

Scheme 28. Asymmetric cascade sulfa-Michael-aldol reaction of 2-mercaptobenzaldehydes with α,β-unsaturated amides

Scheme 29. (a) Catalytic Michael/Horner-Wadsworth-Emmons cascade reaction; (b) control reactions

Scheme 30. Nickel-catalyzed Michael-Henry reaction of 2-mercaptobenzaldehydes with β-nitrostyrenes

Scheme 31. Squaramide-catalyzed asymmetric sulfa-Michael/aldol cascade reaction of 2-mercaptobenzaldehydes and ketones

Scheme 32. Squaramide catalyzed Michael-aldol reaction of 2-mercaptobenzaldehyde with β-indole-β-CF3 enones

Scheme 33. Asymmetric catalytic synthesis of thiochromenes via an acyl transfer-initiated cascade reaction

Scheme 34. Ni-catalyzed asymmetric Michael-Aldol reaction of methyleneindolinones and thiosalicylaldehydes

Scheme 35. Plausible mechanism of Ni-catalyzed Michael- Aldol reaction of methyleneindolinones and thiosalicylaldehydes

Scheme 36. I-Bidine catalyzed asymmetric Michael-aldol reaction of 2-mercaptobenzaldehydes with β-nitrostyrenes

Scheme 37. Catalytic cascade sulfa-Michael/Julia-Kocienski reaction

Scheme 38. Enantioselective squaramide-catalyzed trifluoromethylthiolation-sulfur-Michael/Aldol cascade reaction

Scheme 39. Enantioselective Michael-Aldol cascade reaction of 2-mercaptobenzaldehyde and α,β-unsaturated 7-azaindoline amides

Scheme 40. Formal [3+3] annulation reaction of aminocyclopropanes and thiophenols

Scheme 41. Domino synthesis of thiochromane derivatives via photoinduced electron transfer

Scheme 42. Hydrothiolation/Friedel-Crafts reaction of 1,3-dienes

Scheme 43. Cyclization of [2-(benzylsulfanyl)benzylidene]imi- dazolones

Scheme 44. Ru-catalyzed intramolecular cyclization of propargylic alcohols bearing an (E)-alkene moiety

Scheme 45. Asymmetric Aza-Michael-Michael addition of anilines to nitroolefin enoates

Scheme 46. NHC-catalyzed sulfa-Michael/Michael/lactonization cascade reaction

Scheme 47. Tandem transformation of thioesters for synthesis of thiochromanes

Scheme 48. Squaramide-catalyzed Sulfa-Michael/aldol/lactonization cascade reaction

Scheme 49. Cu-catalyzed hydroamination with anthranils

Scheme 50. Gold-catalyzed double-cyclization of o-(alkynyl)- styrenes for synthesis of thiochromanes and seleno analogues

References 26

[27]	Paladhi, S.; Liu, Y.; Kumar, B. S.; Jung, M.-J.; Park, S. Y.; Yan, H.; Song, C. E. Org. Lett. 2017, 19, 3279. doi: 10.1021/acs.orglett.7b01429
[28]	Li, Y.-P.; Li, Z.-Q.; Zhou, B.; Li, M.-L.; Xue, X.-S.; Zhu, S.-F.; Zhou, Q.-L. ACS Catal. 2019, 9, 6522. doi: 10.1021/acscatal.9b01502
[29]	Chen, C.-Y.; Yang, C.-H.; Hu, W.-P.; Vandavasi, J. K.; Chunga, M.-I.; Wang, J.-J. RSC Adv. 2013, 3, 2710. doi: 10.1039/c2ra22799a
[30]	Muthupandi, P.; Sundaravelu, N.; Sekar, G. J. Org. Chem. 2017, 82, 1936. doi: 10.1021/acs.joc.6b02740 pmid: 28125776
[31]	Le, T. T. H.; Youhei, C.; Le, Q. H.; Nguyen, T. B.; Mac, D. H. Org. Biomol. Chem. 2019, 17, 6355. doi: 10.1039/C9OB01060B
[32]	Velasco, N.; Suárez, A.; Martínez-Lara, F.; Fernández-Rodríguez, M. Á.; Sanz, R.; Suárez-Pantiga, S. J. Org. Chem. 2021, 86, 7078. doi: 10.1021/acs.joc.1c00333
[33]	Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354. pmid: 16895386
[34]	Rios, R.; Sundén, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Córdova, A. Tetrahedron Lett. 2006, 47, 8547. doi: 10.1016/j.tetlet.2006.09.135
[35]	Zu, L.; Wang, J.; Li, H.; Xie, H.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036. doi: 10.1021/ja067781+
[36]	Zu, L.; Xie, H.; Li, H.; Wang, J.; Jiang, W.; Wang, W. Adv. Synth. Catal. 2007, 349, 1882. doi: 10.1002/(ISSN)1615-4169
[37]	Zhao, G.-L.; Vesely, J.; Rios, R.; Ibrahem, I.; Sundén, H.; Córdova, A. Adv. Synth. Catal. 2008, 350, 237. doi: 10.1002/(ISSN)1615-4169
[38]	Dodda, R.; Goldman, J. J.; Mandal, T.; Zhao, C.-G.; Broker, G. A.; Tiekink, E. R. T. Adv. Synth. Catal. 2008, 350, 537. doi: 10.1002/adsc.v350:4
[39]	Dong, X.-Q.; Fang, X.; Tao, H.-Y.; Zhou, X.; Wang, C.-J. Chem. Commun. 2012, 48, 7238. doi: 10.1039/c2cc31891a
[40]	Choudhurya, A. R.; Mukherjee, S. Adv. Synth. Catal. 2013, 355, 1989. doi: 10.1002/adsc.v355.10
[41]	Arai, T.; Yamamoto, Y. Org. Lett. 2014, 16, 1700. doi: 10.1021/ol500361w
[42]	Zhao, B.-L.; Du, D.-M. Asian J. Org. Chem. 2015, 4, 778. doi: 10.1002/ajoc.v4.8
[43]	Zhu, Y.; Dong, Z.; Cheng, X.; Zhong, X.; Liu, X.; Lin, L.; Shen, Z.; Yang, P.; Li, Y.; Wang, H.; Yan, W.; Wang, K.; Wang, R. Org. Lett. 2016, 18, 3546. doi: 10.1021/acs.orglett.6b01498
[44]	Ahlemeyer, N. A.; Birman, V. B. Org. Lett. 2016, 18, 3454. doi: 10.1021/acs.orglett.6b01639 pmid: 27384085
[45]	Arai, T.; Miyazaki, T.; Ogawa, H.; Masu, H. Org. Lett. 2016, 18, 5824. doi: 10.1021/acs.orglett.6b02783
[46]	Arai, T.; Suzuki, T.; Inoue, T.; Kuwano, S. Synlett 2017, 28, 122. doi: 10.1055/s-0036-1588614
[47]	Simlandy, A. K.; Mukherjee, S. J. Org. Chem. 2017, 82, 4851. doi: 10.1021/acs.joc.7b00579 pmid: 28388053
[48]	Zhao, B.-L.; Du, D.-M. Org. Lett. 2017, 19, 1036. doi: 10.1021/acs.orglett.6b03846
[49]	Zhang, Y.-P.; You, Y.; Zhao, J.-Q.; Zhang, X.-M.; Xu, X.-Y.; Yuan, W.-C. J. Org. Chem. 2019, 84, 7984. doi: 10.1021/acs.joc.9b00837
[50]	Wang, M.-M.; Jeon, S.; Waser, J. Org. Lett. 2020, 22, 9123. doi: 10.1021/acs.orglett.0c03528
[51]	Sundaravelu, N.; Nandy, A.; Sekar, G. Org. Lett. 2021, 23, 3115. doi: 10.1021/acs.orglett.1c00806 pmid: 33826352
[52]	Ji, K.; Lu, K.; Huang, J.; Li, Z.-H.; Ke, H.; Chen, Z.-M. Org. Lett. 2021, 23, 8028. doi: 10.1021/acs.orglett.1c03043
[53]	Ji, K.; Lu, K.; Huang, J.; Li, Z.-H.; Ding, T.-M.; Chen, Z.-M. Chem. Commun. 2021, 57, 12639. doi: 10.1039/D1CC05383C
[54]	Zaitseva, E. R.; Sokolov, A. I.; Mikhaylov, A. A.; Baleeva, N. S.; Baranov, M. S.; Smirnov, A. Y. Chem. Heterocycl. Compd. 2022, 58, 477. doi: 10.1007/s10593-022-03115-5
[55]	Fukamizu, K.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2008, 130, 10498. doi: 10.1021/ja8038745 pmid: 18642916
[56]	Wang, X.-F.; An, J.; Zhang, X.-X.; Tan, F.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2011, 13, 808. doi: 10.1021/ol1031188
[57]	Lu, H.; Zhang, J.-L.; Liu, J.-Y.; Li, H.-Y.; Xu, P.-F. ACS Catal. 2017, 7, 7797. doi: 10.1021/acscatal.7b02651
[58]	Ahlemeyer, N. A.; Streff, E. V.; Muthupandi, P.; Birman, V. B. Org. Lett. 2017, 19, 6486. doi: 10.1021/acs.orglett.7b03044 pmid: 29200308
[59]	Mo, Y.; Zhang, X.; Yao, Y.; Duan, C.; Ye, L.; Shi, Z.; Zhao, Z.; Li, X. J. Org. Chem. 2021, 86, 4448. doi: 10.1021/acs.joc.0c02878
[60]	(a) Gu, X.; Meng, L.; Li, M.; Wang, J. Org. Chem. Front. 2021, 8, 1563. doi: 10.1039/D1QO00030F
[1]	(a) Eds.: Andersen, Ø. M.; Markham, K. R. Flavonoids: Chemistry, Biochemistry and Applications, Taylor & Francis, London, 2006.
	(b) Yan, X.; Liu, H.-Q.; Zou, Y.-Q.; Ren, Z.-H. Chin. J. Org. Chem. 2008, 28, 1534. (in Chinese)
	(延玺, 刘会青, 邹永青, 任占华, 有机化学, 2008, 28, 1534.)
	(c) Shao, T.; Li, X.; Qi, C.; Chen, G.; Song, X.; Han, C.; Zheng, C. Chin. J. Org. Chem. 2018, 38, 710. (in Chinese) doi: 10.6023/cjoc201709008
	(邵泰明, 李小宝, 祁翠翠, 陈光英, 宋小平, 韩长日, 郑彩娟, 有机化学, 2018, 38, 710.) doi: 10.6023/cjoc201709008
	(d) Yang, Q.; Wang, Z.; Hor, C. H. H.; Xiao, H.; Bian, Z.; Wang, J. Sci. Adv. 2022, 8, DOI: 10.1126/sciadv.abm9603. doi: 10.1126/sciadv.abm9603
[2]	(a) Brown, M. J.; Carter, P. S.; Fenwick, A. E.; Fosberry, A. P.; Hamprecht, D. W.; Hibbs, M. J.; Jarvest, R. L.; Mensah, L.; Milner, P. H.; O’Hanlon, P. J.; Pope, A. J.; Richardson, C. M.; West, A.; Witty, D. R. Bioorg. Med. Chem. Lett. 2002, 12, 3171. doi: 10.1016/S0960-894X(02)00604-2 pmid: 29626799
	(b) Zimmer, L.; Fournet, G.; Joseph, B.; Guillaumet, G.; Le Bars, D. Nucl. Med. Biol. 2003, 30, 541. pmid: 29626799
	(c) Kanbe, Y.; Kim, M. H.; Nishimoto, M.; Ohtake, Y.; Tsunenari, T.; Taniguchi, K.; Ohizumi, I.; Kaiho, S.; Nabuchi, Y.; Kawata, S.; Morikawa, K.; Jo, J. C.; Kwon, H. A.; Lim, H. S.; Kim, H. Y. Bioorg. Med. Chem. Lett. 2006, 16, 4090. doi: 10.1016/j.bmcl.2006.04.090 pmid: 29626799
	(d) Dalla Via, L.; Magno, S. M.; Gia, O.; Marini, A. M.; Da Settimo, F.; Salerno, S.; La Motta, C.; Simorini, F.; Taliani, S.; Lavecchia, A.; Di Giovanni, C.; Brancato, G.; Barone, V.; Novellino, E. J. Med. Chem. 2009, 52, 5429. doi: 10.1021/jm900627v pmid: 29626799
	(e) Han, X.; Zhong, Y.; Li, S.; Liang, G.; Zhou, G.; Wang, X.; Chen, B.; Song, Y. L. Chem. Pharm. Bull. 2016, 64, 1411. doi: 10.1248/cpb.c16-00366 pmid: 29626799
	(f) Urbatzka, R.; Freitas, S.; Palmeira, A.; Almeida, T.; Moreira, J.; Azevedo, C.; Afonso, C.; Correia-da-Silva, M.; Sousa, E.; Pinto, M.; Vasconcelos, V. Eur. J. Med. Chem. 2018, 151, 272. doi: S0223-5234(18)30279-4 pmid: 29626799
[3]	(a) Nussbaumer, P.; Lehr, P.; Billich, A. J. Med. Chem. 2002, 45, 4310. pmid: 12213072
	(b) Horvath, A.; Nussbaumer, P.; Wolff, B.; Billich, A. J. Med. Chem. 2004, 47, 4268. doi: 10.1021/jm0407916 pmid: 12213072
	(c) Kataoka, T.; Watanabe, S.; Mori, E.; Kadomoto, R.; Tanimura, S.; Kohno, M. Bioorg. Med. Chem. 2004, 12, 2397. doi: 10.1016/j.bmc.2004.02.002 pmid: 12213072
[4]	(a) Kitani, S.; Sugawara, K.; Tsutsumi, K.; Morimoto, T.; Kakiuchi, K. Chem. Commun. 2008, 2103. pmid: 30023661
	(b) Hikage, S.; Nishiyama, Y.; Sasaki, Y.; Tanimoto, H.; Morimoto, T.; Kakiuchi, K. ACS Omega 2017, 2, 2300. doi: 10.1021/acsomega.7b00250 pmid: 30023661
[5]	(a) Quaglia, W.; Giannella, M.; Piergentili, A.; Pigini, M.; Brasili, L.; Di Toro, R.; Rossetti, L.; Spampinato, S.; Melchiorre, C. J. Med. Chem. 1998, 41, 1557. pmid: 9572880
[60]	(b) Yang. Q.; Li, S.; Wang, J. ChemCatChem 2020, 12, 3202. doi: 10.1002/cctc.v12.12
[61]	Virumbrales, C.; El-Remaily, M. A. E. A. A. A.; Suárez-Pantiga, S.; Fernández-Rodríguez, M. A.; Rodríguez, F.; Sanz, R. Org. Lett. 2022, 24, 8077. doi: 10.1021/acs.orglett.2c03411
[5]	(b) Liu, R.; Mabury, S. A. Environ. Sci. Technol. 2018, 52, 10089. doi: 10.1021/acs.est.8b02457 pmid: 9572880
	(c) Zhan, T.; Pan, L.; Liu, Z.; Chen, J.; Ge, Z.; Lu, L.; Zhang, X.; Cui, S.; Zhang, C.; Liu, W.; Zhuang, S. Environ. Sci. Technol. 2018, 52, 11904. pmid: 9572880
	(d) Li, J.; Lam, J. C. W.; Li, W.; Du, B.; Chen, H.; Zeng, L. Environ. Sci. Technol. 2019, 53, 10969. doi: 10.1021/acs.est.9b03127 pmid: 9572880
[6]	Weerasekare, G. M.; Berlin, K. D.; Sunkara, H.; Ford, W. T. Phosphorus Sulfur 2003, 178, 993. doi: 10.1080/10426500307852
[7]	Liu, J.; Hu, T.; Li, Z.; Wei, X.; Hu, X.; Gao, H.; Liu, G.; Yi, Y.; Yamada-Takamura, Y.; Lee, C. S.; Wang, P.; Wang, Y. J. Phys. Chem. Lett. 2019, 10, 1888. doi: 10.1021/acs.jpclett.9b00512
[8]	(a) Nibbs, A. E.; Scheidt, K. A. Eur. J. Org. Chem. 2012, 2012, 449. doi: 10.1002/ejoc.v2012.3
	(b) Meng, L.; Wang, J. Synlett 2016, 27, 656. doi: 10.1055/s-00000083
	(c) Yang, Q.; Guo, R.; Wang, J. Asian J. Org. Chem. 2019, 8, 1742. doi: 10.1002/ajoc.v8.10
	(d) Xiong, L.; Hu, H.; Wei, C.; Yu, B. Eur. J. Org. Chem. 2020, 2020, 1588. doi: 10.1002/ejoc.201901581
	(e) He, Q.-J.; So, C.-M.; Bian, Z.-X.; Hayashi, T.; Wang, J. Chem. Asian. J. 2015, 10, 540. doi: 10.1002/asia.201403290
	(f) Lyu, L.-Y.; Jin, M. Y.; He, Q.-J.; Xie. H.; Bian, Z.-X.; Wang, J. Org. Biomol. Chem. 2016, 14, 8088. doi: 10.1039/C6OB01355D
	(g) Yang, Q.; Wang, Y.; Luo, S.; Wang, J. Angew. Chem., Int. Ed. 2019, 58, 5343. doi: 10.1002/anie.v58.16
	(h) Cai, B.; Yang, Q.; Meng, L.; Wang, J. Chin. J. Chem. 2021, 39, 1606. doi: 10.1002/cjoc.v39.6
	(g) Meng, L.; Liu, H.; Lin, Z.; Wang, J. Org. Lett. 2022, 24, 5890. doi: 10.1021/acs.orglett.2c01922
[9]	(a) Schneller, S. W. InAdvances in Heterocyclic Chemistry, Vol.18, Eds.: Katritzky, A. R.; Boulton, A. J., United States, 1975, pp. 59-97.
	(b) Bondock, S.; Metwally, M. A. J. Sulfur Chem. 2008, 29, 623. doi: 10.1080/17415990802382882
[10]	(a) Dike, S. Y.; Ner, D. H.; Kumar, A. Bioorg. Med. Chem. Lett. 1991, 1, 383. doi: 10.1016/S0960-894X(00)80260-7 pmid: 10956195
	(b) van Vliet, L. A.; Rodenhuis, N.; Dijkstra, D.; Wikstrom, H.; Pugsley, T. A.; Serpa, K. A.; Meltzer, L. T.; Heffner, T. G.; Wise, L. D.; Lajiness, M. E.; Huff, R. M.; Svensson, K.; Sundell, S.; Lundmark, M. J. Med. Chem. 2000, 43, 2871. pmid: 10956195
	(c) Choi, E. J.; Lee, J. I.; Kim, G. H. Int. J. Mol. Med. 2012, 29, 252. pmid: 10956195
	(d) Song, J.; Jones, L. M.; Chavarria, G. E.; Charlton-Sevcik, A. K.; Jantz, A.; Johansen, A.; Bayeh, L.; Soeung, V.; Snyder, L. K.; Lade, S. D., Jr.; Chaplin, D. J.; Trawick, M. L.; Pinney, K. G. Bioorg. Med. Chem. Lett. 2013, 23, 2801. doi: 10.1016/j.bmcl.2012.12.025 pmid: 10956195
	(e) Song, Y. L.; Wu, F.; Zhang, C. C.; Liang, G. C.; Zhou, G.; Yu, J. J. Bioorg. Med. Chem. Lett. 2015, 25, 259. doi: 10.1016/j.bmcl.2014.11.056 pmid: 10956195
[11]	(a) Clayton, S. E.; Gabbutt, C. D.; Hepworth, J. D.; Heron, B. M. Tetrahedron 1993, 49, 939. doi: 10.1016/S0040-4020(01)80335-5
	(b) Kumar, P.; Rao, A. T.; Pandey, B. Synth. Commun. 1994, 24, 3297. doi: 10.1080/00397919408010253
	(c) Konieczny, M. K.; Horowska, B.; Kunikowski, A.; Konopa, J.; Wierzba, K.; Yamada, Y.; Asao, T. J. Org. Chem. 1999, 64, 359. doi: 10.1021/jo980586w
	(d) Cui, D.-M.; Kawamura, M.; Shimada, S.; Hayashi, T.; Tanaka, M. Tetrahedron Lett. 2003, 44, 4007. doi: 10.1016/S0040-4039(03)00855-4
	(e) Li, J.; Li, H.; Li, H.; Xiao, L. J. Chem. Res. 2004, 6, 394.
[12]	Vaghoo, H.; Prakash, G. K. S.; Narayanan, A.; Choudhary, R.; Paknia, F.; Mathew, T.; Olah, G. A. Org. Lett. 2015, 17, 6170. doi: 10.1021/acs.orglett.5b03172
[13]	Sangeetha, S.; Muthupandi, P.; Sekar, G. Org. Lett. 2015, 17, 6006. doi: 10.1021/acs.orglett.5b02977
[14]	Bouisseau, A.; Glancy, J.; Willis, M. C. Org. Lett. 2016, 18, 5676. pmid: 27779887
[15]	Guo, F.; Jeffries, M. C.; Graves, B. N.; Graham, S. A.; Pollard, D. A.; Pang, G.; Chen, H. Y. Tetrahedron 2017, 73, 5745. doi: 10.1016/j.tet.2017.08.012
[16]	Chen, X.-L.; Tang, B.-C.; He, C.; Ma, J.-T.; Zhuang, S.-Y.; Wu, Y.-D.; Wu, A.-X. Chem. Commun. 2020, 53, 13653.
[17]	Nandy, A.; Sekar, G. J. Org. Chem. 2022, 87, 7536. doi: 10.1021/acs.joc.2c00425
[18]	Meng, L.; Jin, M. Y.; Wang, J. Org. Lett. 2016, 18, 4986. doi: 10.1021/acs.orglett.6b02453
[19]	Luo, S.; Meng, L.; Yang, Q.; Wang, J. Synlett 2018, 29, 2071. doi: 10.1055/s-0037-1610225
[20]	Vila, C.; Hornillos, V.; Fananas-Mastral, M.; Feringa, B. L. Chem. Commun. 2013, 49, 5933. doi: 10.1039/c3cc43105c
[21]	Trost, B. M.; Gnanamani, E.; Kalnmals, C. A.; Hung, C.; Tracy, J. S. J. Am. Chem. Soc. 2019, 141, 1489. doi: 10.1021/jacs.8b13367
[22]	Meng, L.; Ngai, K. Y.; Chang, X.; Lin, Z.; Wang, J. Org. Lett. 2020, 22, 1155. doi: 10.1021/acs.orglett.0c00005
[23]	Zhao, D.; Beiring, B.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 8454. doi: 10.1002/anie.v52.32
[24]	Xiong, D.; Zhou, W.; Lu, Z.; Zeng, S.; Wang, J. Chem. Commun. 2017, 53, 6844. doi: 10.1039/C7CC03939E
[25]	Kerr, M. S.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298. doi: 10.1021/ja027411v
[26]	Li, W.; Liu, X.; Hao, X.; Hu, X.; Chu, Y.; Cao, W.; Qin, S.; Hu, C.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2011, 133, 15268. doi: 10.1021/ja2056159

硫代黄烷酮类衍生物的合成研究进展