Abstract
A practical and efficient synthetic route to construct a variety of 3-arylselenenyl/3-arylthio spiro[4.5]trienones was developed using Selectfluor reagent as a mild oxidant. This reaction proceeds via a sequence of electrophilic cation addition, spirocyclization and dearomatization, then offers an approach to introduce Se/S-centered cation into the C–C triple bonds. The utility of this protocol were justified by the excellent compatibility of a wide range of functional groups, good yields and scalability under mild reaction conditions.
Funding source: Natural Science Foundation in Henan Province Department of Education
Award Identifier / Grant number: 21A150016
Funding source: Innovative Funds Plan of Henan University of Technology
Award Identifier / Grant number: 2020ZKCJ29
Funding source: Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology
Award Identifier / Grant number: 2017RCJH08
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: This work was supported by the Natural Science Foundation in Henan Province Department of Education (No. 21A150016), the Innovative Funds Plan of Henan University of Technology (No. 2020ZKCJ29), and the Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology (No. 2017RCJH08).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Cai, Y. S., Guo, Y. W., Krohn, K. Nat. Prod. Rep. 2010, 27, 1840–1870; https://doi.org/10.1039/c0np00031k.Search in Google Scholar PubMed
2. Gravel, E., Poupon, E. Nat. Prod. Rep. 2010, 27, 32–56; https://doi.org/10.1039/b911866g.Search in Google Scholar PubMed
3. Antunes, E. M., Copp, B. R., Davier-Coleman, M. T., Samaai, T. Nat. Prod. Rep. 2005, 22, 62–72; https://doi.org/10.1039/b407299p.Search in Google Scholar PubMed
4. Yoneda, K., Yamagata, E., Nakanishi, T., Nagashima, T., Kawasaki, I., Yoshida, T., Mori, H., Miura, I. Photochemistry 1984, 23, 2068–2069; https://doi.org/10.1016/s0031-9422(00)84976-6.Search in Google Scholar
5. Yugandhar, D., Nayak, V. L., Archana, S., Shekar, K. C., Srivastava, A. K. Eur. J. Med. Chem. 2015, 101, 348–357; https://doi.org/10.1016/j.ejmech.2015.06.050.Search in Google Scholar PubMed
6. Winkler, M., Maynadier, M., Wein, S., Lespinasse, M., Boumis, G., Miele, A. E., Vial, H., Wong, Y. Org. Biomol. Chem. 2015, 13, 2064–2077; https://doi.org/10.1039/c4ob02459a.Search in Google Scholar PubMed
7. Leon, R., Jawalekar, A., Redert, T., Gaunt, M. J. Chem. Sci. 2011, 2, 1487–1490; https://doi.org/10.1039/c1sc00218j.Search in Google Scholar
8. Jia, M. Q., You, S. L. Chem. Commun. 2012, 48, 6363–6636; https://doi.org/10.1039/c2cc32783j.Search in Google Scholar PubMed
9. Roche, S. T., Porco, J. A. Angew. Chem. Int. Ed. 2011, 50, 4068–4409; https://doi.org/10.1002/anie.201006017.Search in Google Scholar PubMed PubMed Central
10. Zhuo, C. X., Zhang, W., You, S. L. Angew. Chem. Int. Ed. 2012, 51, 12662–12686; https://doi.org/10.1002/anie.201204822.Search in Google Scholar PubMed
11. Reddy, C. R., Prajapti, S. K., Warudikar, K., Ranjan, R., Rao, B. B. Org. Biomol. Chem. 2017, 15, 3130–3051; https://doi.org/10.1039/c7ob00405b.Search in Google Scholar PubMed
12. Dohi, T., Maruyama, A., Yoshimura, M., Morimoto, K., Tohma, H., Kita, Y. Angew. Chem. Int. Ed. 2005, 44, 6193–9196; https://doi.org/10.1002/anie.200501688.Search in Google Scholar PubMed
13. Magdziak, D., Meek, S. J., Pettus, T. R. R. Chem. Rev. 2004, 104, 1383–1429; https://doi.org/10.1021/cr0306900.Search in Google Scholar PubMed
14. Pouységu, L., Deffieux, D., Quideau, S. Tetrahedron 2010, 66, 2235–2261.10.1016/j.tet.2009.12.046Search in Google Scholar
15. Yugandhar, D., Kuriakose, S., Nanubolu, J. B., Srivastava, A. K. Org. Lett. 2016, 18, 1040–1043; https://doi.org/10.1021/acs.orglett.6b00164.Search in Google Scholar PubMed
16. Yu, Q. F., Zhang, Y. H., Yin, W., Tang, B. X., Tang, R. Y., Zhang, P., Li, J. H. J. Org. Chem. 2008, 73, 3568–3661; https://doi.org/10.1021/jo800328a.Search in Google Scholar PubMed
17. Yin, Q., You, S. L. Org. Lett. 2012, 14, 3526–3529; https://doi.org/10.1021/ol301531z.Search in Google Scholar PubMed
18. Wang, L. J., Zhu, H. T., Qiu, Y. F., Liu, X. Y., Liang, Y. M. Org. Biomol. Chem. 2014, 12, 643–650; https://doi.org/10.1039/c3ob42020e.Search in Google Scholar PubMed
19. Tnay, Y. L., Chen, C., Chua, Y. Y., Zhang, L., Chiba, S. Org. Lett. 2012, 14, 3550–3553; https://doi.org/10.1021/ol301583y.Search in Google Scholar PubMed
20. Wu, Q. F., Liu, W. B., Zhuo, C. X., Rong, Z. Q., Ye, K. Y., You, S. L. Angew. Chem. Int. Ed. 2011, 50, 4455–4458; https://doi.org/10.1002/anie.201100206.Search in Google Scholar PubMed
21. Rousseaux, S., García-ortanet, J., Del Aguila Sanchez, M. A., Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 9282–9285; https://doi.org/10.1021/ja203644q.Search in Google Scholar PubMed PubMed Central
22. Pigge, F. C., Coniglio, J. J., Dalvi, R. J. Am. Chem. Soc. 2006, 128, 3498–3499; https://doi.org/10.1021/ja058342y.Search in Google Scholar PubMed
23. Matsuura, B. S., Condie, A. G., Buff, R. C., Karahalis, G. J., Stephenson, C. R. J. Org. Lett. 2011, 13, 6320–6632; https://doi.org/10.1021/ol202881q.Search in Google Scholar PubMed PubMed Central
24. Bansode, A. H., Shaikh, S. R., Gonnade, R. G., Patil, N. T. Chem. Commun. 2017, 53, 9081–9084; https://doi.org/10.1039/c7cc04010e.Search in Google Scholar PubMed
25. Zheng, D., Yu, J., Wu, J. Angew. Chem. Int. Ed. 2016, 55, 11925–11929; https://doi.org/10.1002/anie.201607292.Search in Google Scholar PubMed
26. Yang, X. L., Long, Y., Chen, F., Han, B. Org. Chem. Front. 2016, 3, 184–189; https://doi.org/10.1039/c5qo00352k.Search in Google Scholar
27. Ouyang, X. H., Song, R. J., Liu, B., Li, J. H. Chem. Commun. 2016, 52, 2573–2576; https://doi.org/10.1039/c5cc08952b.Search in Google Scholar PubMed
28. Ni, S., Cao, J., Mei, H., Han, J., Li, S., Pan, Y. Green Chem. 2016, 18, 3935–3939; https://doi.org/10.1039/c6gc01027j.Search in Google Scholar
29. Schumacher, R. F., Rosario, A. R., Souza, A. C. G., Menezes, P. H., Zeni, G. Org. Lett. 2010, 12, 1952–1955; https://doi.org/10.1021/ol1003753.Search in Google Scholar PubMed
30. Godoi, B., Schumacher, R. F., Zeni, G. Chem. Rev. 2011, 111, 2937–2980; https://doi.org/10.1021/cr100214d.Search in Google Scholar PubMed
31. Zhang, X., Larock, R. C. J. Am. Chem. Soc. 2005, 127, 12230–12231; https://doi.org/10.1021/ja053079m.Search in Google Scholar PubMed
32. Tang, B. X., Tang, D. J., Tang, S., Yu, O. F., Zhang, Y. H., Liang, Y., Zhong, P., Li, J. H. Org. Lett. 2008, 10, 1063–1066; https://doi.org/10.1021/ol703050z.Search in Google Scholar PubMed
33. Wen, J., Wei, W., Xue, S., Yang, D., Lou, Y., Gao, C., Wang, H. J. Org. Chem. 2015, 80, 4966–4972; https://doi.org/10.1021/acs.joc.5b00361.Search in Google Scholar PubMed
34. Hua, H. L., He, Y. T., Qiu, Y. F., Li, Y. X., song, B., Gao, P., Song, X. R., Guo, D. H., Liu, X. Y., Liang, Y. M. Chem. Eur. J. 2015, 21, 1468–1473; https://doi.org/10.1002/chem.201405672.Search in Google Scholar PubMed
35. Yang, W. C., Zhang, M. M., Feng, J. G. Adv. Synth. Catal. 2020, 362, 4446–4461; https://doi.org/10.1002/adsc.202000636.Search in Google Scholar
36. Tang, B. X., Zhang, Y. H., Song, R. J., Tang, D. J., Deng, G. B., Wang, Z. Q., Xie, Y. X., Xia, Y. Z., Li, J. H. J. Org. Chem. 2012, 77, 2837–2849; https://doi.org/10.1021/jo300037n.Search in Google Scholar PubMed
37. Yu, Q. F., Zhang, Y. H., Yin, Q., Tang, B. X., Tang, R. Y., Zhang, P., Li, J. H. J. Org. Chem. 2008, 73, 3658–3661; https://doi.org/10.1021/jo800328a.Search in Google Scholar PubMed
38. Liu, T., Li, Y., Jiang, L., Wang, J., Jin, K., Zhang, R., Duan, C. Org. Biomol. Chem. 2020, 18, 1933–1939; https://doi.org/10.1039/d0ob00057d.Search in Google Scholar PubMed
39. Nair, A. M., Shinde, A. H., Kumar, S., Volla, C. M. R. Chem. Commun. 2020, 56, 12367–12370; https://doi.org/10.1039/d0cc04800c.Search in Google Scholar PubMed
40. Tang, B. X., Yin, Q., Tang, R. Y., Li, J. H. J. Org. Chem. 2008, 73, 9008–9011; https://doi.org/10.1021/jo8018297.Search in Google Scholar PubMed
41. Yu, K., Kong, X., Yang, J., Li, G., Xu, B., Chen, Q. J. Org. Chem. 2021, 86, 917–928; https://doi.org/10.1021/acs.joc.0c02429.Search in Google Scholar PubMed
42. Chen, P., Xie, J., Chen, Z., Xiong, B. Q., Liu, Y., Yang, C. A., Tang, K. W. Adv. Synth. Catal. 2021, 363, 4440–4446; https://doi.org/10.1002/adsc.202100852.Search in Google Scholar
43. Ouyang, X. H., Song, R. J., Li, Y., Liu, B., Li, J. H. J. Org. Chem. 2014, 79, 4582–4589; https://doi.org/10.1021/jo5005982.Search in Google Scholar PubMed
44. Liu, Y., Wang, Q. L., Zhou, C. S., Xiong, B. Q., Zhang, P. L., Yang, C., Tang, K. W. J. Org. Chem. 2018, 83, 2210–2218; https://doi.org/10.1021/acs.joc.7b03104.Search in Google Scholar PubMed
45. Reddy, C. R., Kolgave, D. H., Subbarao, M., Aila, M., Prajapti, S. K. Org. Lett. 2020, 22, 5342–5346; https://doi.org/10.1021/acs.orglett.0c01588.Search in Google Scholar PubMed
46. Wei, W. T., Song, R. J., Ouyang, X. H., Li, Y., Li, H. B., Li, J. H. Org. Chem. Front. 2014, 1, 484–489; https://doi.org/10.1039/c4qo00006d.Search in Google Scholar
47. Wang, C. S., Roisnel, T., Dixneuf, P. H., Soulé, J. F. Adv. Synth. Catal. 2019, 361, 445–450; https://doi.org/10.1002/adsc.201801203.Search in Google Scholar
48. Manna, S., Ashwathappa, P. K. S., Prabhu, K. R. Chem. Commun. 2020, 56, 13165–13168; https://doi.org/10.1039/d0cc01217c.Search in Google Scholar PubMed
49. Li, M., Song, R. J., Li, J. H. Chin. J. Chem. 2017, 35, 299–302; https://doi.org/10.1002/cjoc.201600749.Search in Google Scholar
50. Reddy, C. R., Yarlagadda, S., Ramesh, B., Reddy, M. R., Sridhar, B., Reddy, B. V. S. Eur. J. Org. Chem. 2017, 2017, 2332–2337; https://doi.org/10.1002/ejoc.201700058.Search in Google Scholar
51. Wang, L. J., Wang, A. Q., Xia, Y., Wu, X. X., Liu, X. Y., Liang, Y. M. Chem. Commun. 2014, 50, 13998–14001; https://doi.org/10.1039/c4cc06923d.Search in Google Scholar PubMed
52. Zeng, F. L., Chen, X. L., Sun, K., Zhu, H. L., Yuan, X. Y., Liu, Y., Qu, L. B., Zhao, Y. F., Yu, B. Org. Chem. Front. 2021, 8, 760–766; https://doi.org/10.1039/d0qo01410a.Search in Google Scholar
53. Yang, X. H., Ouyang, X. H., Wei, W. T., Song, R. J., Li, J. H. Adv. Synth. Catal. 2015, 357, 1161–1166; https://doi.org/10.1002/adsc.201400895.Search in Google Scholar
54. Chen, Y., Chen, Y. J., Guan, Z., He, Y. H. Tetrahedron 2019, 75, 130763; https://doi.org/10.1016/j.tet.2019.130763.Search in Google Scholar
55. Wu, L. J., Tan, F. L., Li, M., Song, R. J., Li, J. H. Org. Chem. Front. 2017, 4, 350–353; https://doi.org/10.1039/c6qo00691d.Search in Google Scholar
56. Gao, P., Zhang, W., Zhang, Z. Org. Lett. 2016, 18, 5820–5823; https://doi.org/10.1021/acs.orglett.6b02781.Search in Google Scholar PubMed
57. Nair, A. M., Halder, I., Khan, S., Volla, C. M. R. Adv. Synth. Catal. 2020, 362, 224–229; https://doi.org/10.1002/adsc.201901321.Search in Google Scholar
58. Liu, Y., Wang, Q. L., Xiong, B. Q., Zhang, P. L., Yang, C. A., Gong, Y. X., Liao, J., Zhou, Q. Synlett 2018, 29, 2396–2403; https://doi.org/10.1055/s-0037-1609948.Search in Google Scholar
59. Liu, Y., Wang, Q. L., Chen, Z., Zhou, Q., Xiong, B. Q., Zhang, P. L., Tang, K. W. Chem. Commun. 2019, 55, 12212–12215; https://doi.org/10.1039/c9cc05949k.Search in Google Scholar PubMed
60. Jin, D. P., Gao, P., Chen, D. Q., Chen, S., Wang, J., Liu, X. Y., Liang, Y. M. Org. Lett. 2016, 18, 3486–3489; https://doi.org/10.1021/acs.orglett.6b01702.Search in Google Scholar PubMed
61. Brutchey, R. L. Acc. Chem. Res. 2015, 48, 2918–2926; https://doi.org/10.1021/acs.accounts.5b00362.Search in Google Scholar PubMed
62. Modha, S. G., Mehtab, V. P., der Eycken, E. V. V. Chem. Soc. Rev. 2013, 42, 5042–5055; https://doi.org/10.1039/c3cs60041f.Search in Google Scholar PubMed
63. Fourmigue, M., Dhaka, A. Coord. Chem. Rev. 2020, 403, 213084–213100; https://doi.org/10.1016/j.ccr.2019.213084.Search in Google Scholar
64. Chen, Z., Lai, H., Hou, L., Chen, T. Chem. Commun. 2020, 56, 179–196; https://doi.org/10.1039/c9cc07683b.Search in Google Scholar PubMed
65. Frieben, E. E., Amin, S., Sharma, A. K. J. Med. Chem. 2019, 62, 5261–5275; https://doi.org/10.1021/acs.jmedchem.8b01698.Search in Google Scholar PubMed
66. Csonka, A., Kincses, A., Nove, M., Vadas, Z., Spengler, G., Csonka, A., Sanmartin, C., Sanmartin, C., Dominguez-Alvarez, E. Anticancer Res. 2019, 39, 3777–3783; https://doi.org/10.21873/anticanres.13526.Search in Google Scholar PubMed
67. Vahter, J., Viht, K., Uri, A., Manoharan, G. B., Enkvist, E. Bioorg. Med. Chem. 2018, 26, 5062–5068; https://doi.org/10.1016/j.bmc.2018.09.003.Search in Google Scholar PubMed
68. Tian, M., Yang, Y., Avila, F. W., Fish, T., Yuan, H., Hui, M., Thannhauser, T. W., Li, L., Tian, M., Pan, S. J. Agric. Food Chem. 2018, 66, 8036–8044; https://doi.org/10.1021/acs.jafc.8b03396.Search in Google Scholar PubMed
69. Wang, X. Y., Zhong, Y. F., Mo, Z. Y., Wu, S. H., Xu, Y. L., Tang, H. T., Pan, Y. M. Adv. Synth. Catal. 2021, 363, 208–214; https://doi.org/10.1002/adsc.202001192.Search in Google Scholar
70. Song, Z., Ding, C., Wang, S., Dai, Q., Sheng, Y., Zheng, Z., Liang, G. Chem. Commun. 2020, 56, 1847–1850; https://doi.org/10.1039/c9cc09001k.Search in Google Scholar PubMed
71. Ai, Z., Xiao, J., Li, Y., Guo, B., Du, Y., Zhao, K. Org. Chem. Front. 2020, 7, 3935–3940; https://doi.org/10.1039/d0qo01175d.Search in Google Scholar
72. Ghosh, P., Chhetri, G., Perl, E., Das, S. Adv. Synth. Catal. 2021, 363, 2148–2156; https://doi.org/10.1002/adsc.202001426.Search in Google Scholar
73. Sun, K., Wang, S., Feng, R., Zhang, Y., Wang, X., Zhang, Z., Zhang, B. Org. Lett. 2019, 21, 2052–2055; https://doi.org/10.1021/acs.orglett.9b00240.Search in Google Scholar PubMed
74. Kosso, A. R. O., Kabri, Y., Broggi, J., Redon, S., Vanelle, P. J. Org. Chem. 2020, 85, 3071–3081; https://doi.org/10.1021/acs.joc.9b02963.Search in Google Scholar PubMed
75. Brahmachari, G., Bhowmick, A., Karmakar, I. J. Org. Chem. 2021, 86, 9658–9669; https://doi.org/10.1021/acs.joc.1c00919.Search in Google Scholar PubMed
76. Cui, H., Wei, W., Yang, D., Zhang, J., Xu, Z., Wen, J., Wang, H. RSC Adv. 2015, 5, 84657–84661; https://doi.org/10.1039/c5ra16548b.Search in Google Scholar
77. Qian, P. C., Liu, Y., Song, R. J., Xiang, J. N., Li, J. H. Synlett 2015, 26, 1213–1216.10.1055/s-0034-1380573Search in Google Scholar
78. Skubi, K. L., Blum, T. R., Yoon, T. P. Chem. Rev. 2016, 116, 10035–10074; https://doi.org/10.1021/acs.chemrev.6b00018.Search in Google Scholar PubMed PubMed Central
79. Romero, N. A., Nicewicz, D. A. Chem. Rev. 2016, 116, 10075–10166; https://doi.org/10.1021/acs.chemrev.6b00057.Search in Google Scholar PubMed
80. Xuan, J., Xiao, W. J. Angew. Chem. Int. Ed. 2012, 51, 6828–6838; https://doi.org/10.1002/anie.201200223.Search in Google Scholar PubMed
81. Nicewicz, D. A., MacMillan, D. W. C. Science 2008, 322, 77–80; https://doi.org/10.1126/science.1161976.Search in Google Scholar PubMed PubMed Central
82. Yoon, T. P., Ischay, M. A. Du J. Nat. Chem. 2010, 2, 527–532; https://doi.org/10.1038/nchem.687.Search in Google Scholar PubMed
83. Shi, L., Xia, W. Chem. Soc. Rev. 2012, 41, 7687–7697; https://doi.org/10.1039/c2cs35203f.Search in Google Scholar PubMed
84. Wei, W., Cui, H., Yang, D., Yue, H., He, C., Zhang, Y., Wang, H. Green Chem. 2017, 19, 5608–5613; https://doi.org/10.1039/c7gc02330h.Search in Google Scholar
85. Sahoo, H., Mandal, A., Dana, S., Baidya, M. Adv. Synth. Catal. 2018, 360, 1099–1103; https://doi.org/10.1002/adsc.201701410.Search in Google Scholar
86. Zhang, N., Zuo, H., Xu, C., Pan, J., Sun, J., Guo, C. Chin. Chem. Lett. 2020, 31, 337–340; https://doi.org/10.1016/j.cclet.2019.06.008.Search in Google Scholar
87. Wang, H., Gao, X., Lv, Z., Abdelilah, T., Lei, A. Chem. Rev. 2019, 119, 6769–6787; https://doi.org/10.1021/acs.chemrev.9b00045.Search in Google Scholar PubMed
88. Moeller, K. D. Chem. Rev. 2018, 118, 4817–4833; https://doi.org/10.1021/acs.chemrev.7b00656.Search in Google Scholar PubMed
89. Yan, M., Kawamata, Y., Baran, P. S. Chem. Rev. 2017, 117, 13230–13319; https://doi.org/10.1021/acs.chemrev.7b00397.Search in Google Scholar PubMed PubMed Central
90. Waldvogel, S. R., Lips, S., Selt, M., Riehl, B., Kampf, C. J. Chem. Rev. 2018, 118, 6706–6765; https://doi.org/10.1021/acs.chemrev.8b00233.Search in Google Scholar PubMed
91. Zhao, Y., Xia, W. Chem. Soc. Rev. 2018, 47, 2591–2608; https://doi.org/10.1039/c7cs00572e.Search in Google Scholar PubMed
92. Yan, M., Kawamata, Y., Baran, P. S. Angew. Chem. Int. Ed. 2018, 57, 4149–4155; https://doi.org/10.1002/anie.201707584.Search in Google Scholar PubMed PubMed Central
93. Hua, J., Fang, Z., Bian, M., Ma, T., Yang, M., Xu, J., Liu, C. K., He, W., Zhu, N., Yang, Z., Guo, K. ChemSusChem 2020, 13, 2053–2059; https://doi.org/10.1002/cssc.202000098.Search in Google Scholar PubMed
94. Recchi, A. M. S., Rosa, P. H. P., Back, D. F., Zeni, G. Org. Biomol. Chem. 2020, 18, 3544–3551; https://doi.org/10.1039/d0ob00609b.Search in Google Scholar PubMed
95. Sahoo, H., Grandhi, G. S., Ramakrishna, I., Baidya, M. Org. Biomol. Chem. 2019, 17, 10163–10166; https://doi.org/10.1039/c9ob02177a.Search in Google Scholar PubMed
96. Nyffeler, P. T., Durón, S. G., Burkart, M. D., Vincent, S. P., Wong, C. H. Angew. Chem. Int. Ed. 2005, 44, 192–212; https://doi.org/10.1002/anie.200400648.Search in Google Scholar PubMed
97. Liu, P., Gao, Y., Gu, W., Shen, Z., Sun, P. J. Org. Chem. 2015, 80, 11559–11565; https://doi.org/10.1021/acs.joc.5b01961.Search in Google Scholar PubMed
98. Li, J. L., Lin, E., Han, X. L., Li, Q., Wang, H. Org. Lett. 2019, 21, 4255–4258; https://doi.org/10.1021/acs.orglett.9b01428.Search in Google Scholar PubMed
99. Xu, P., Guo, S., Wang, L., Tang, P. Angew. Chem., Int. Ed. 2014, 53, 5955–5958; https://doi.org/10.1002/anie.201400225.Search in Google Scholar PubMed
100. Xie, L. Y., Qu, J., Peng, S., Liu, K. J., Wang, Z., Ding, M. H., Wang, Y., Cao, Z., He, W. M. Green Chem. 2018, 20, 760–764; https://doi.org/10.1039/c7gc03106h.Search in Google Scholar
101. Ban, Y. L., You, L., Feng, K. W., Ma, F. C., Jin, X. L., Liu, Q. J. Org. Chem. 2021, 86, 5274–5283; https://doi.org/10.1021/acs.joc.1c00167.Search in Google Scholar PubMed
102. Yang, L., Ma, Y., Song, F., You, J. Chem. Commun. 2014, 50, 3024–3026; https://doi.org/10.1039/c3cc49851d.Search in Google Scholar PubMed
103. Niu, L., Liu, J., Liang, X. A., Wang, S., Lei, A. Nat. Commun. 2019, 10, 1–7; https://doi.org/10.1038/s41467-019-08413-9.Search in Google Scholar PubMed PubMed Central
104. Xavier, M. C. D. F., Sandagorda, E. M. A., Neto, J. S. S., Schumacher, R. F., Silva, M. S. RSC Adv. 2020, 10, 13975–13983; https://doi.org/10.1039/d0ra01907k.Search in Google Scholar PubMed PubMed Central
105. Xie, L. Y., Peng, S., Liu, F., Yi, J. Y., Wang, M., Tang, Z., Xu, X., He, W. M. Adv. Synth. Catal. 2018, 360, 4259–4264; https://doi.org/10.1002/adsc.201800918.Search in Google Scholar
106. Kong, Y., Sun, X., Weng, J. Chin. J. Org. Chem. 2020, 40, 2641–2657; https://doi.org/10.6023/cjoc202004005.Search in Google Scholar
107. Wang, X., Wang, Q., Xue, Y., Sun, K., Wu, L., Zhang, B. Chem. Commun. 2020, 56, 4436–4439; https://doi.org/10.1039/d0cc01079k.Search in Google Scholar PubMed
108. Galloway, J. D., Mai, D. N., Baxter, R. D. Org. Lett. 2017, 19, 5772–5775; https://doi.org/10.1021/acs.orglett.7b02706.Search in Google Scholar PubMed
109. Liang, X. A., Niu, L., Wang, S., Liu, J., Lei, A. Org. Lett. 2019, 21, 2441–2444; https://doi.org/10.1021/acs.orglett.9b00744.Search in Google Scholar PubMed
110. Kong, Y., Yu, W., Liu, X., Weng, J. Chin. Chem. Lett. 2020, 31, 3245–3249; https://doi.org/10.1016/j.cclet.2020.05.022.Search in Google Scholar
111. Fei, H., Xu, Z., Wu, H., Zhu, L., Jalani, H. B., Li, G., Fu, Y., Lu, H. Org. Lett. 2020, 22, 2651–2656; https://doi.org/10.1021/acs.orglett.0c00620.Search in Google Scholar PubMed
112. Zhao, H., Jin, J. Org. Lett. 2019, 21, 6179–6184; https://doi.org/10.1021/acs.orglett.9b01635.Search in Google Scholar PubMed
113. Mai, W. P., Yuan, J. W., Zhu, J. L., Li, Q. Q., Yang, L. R., Xiao, Y. M., Mao, P., Qu, L. B. ChemistrySelect 2019, 4, 11066–11070; https://doi.org/10.1002/slct.201903478.Search in Google Scholar
114. Yuan, J., Zeng, F., Mai, W., Yang, L., Xiao, Y., Mao, P., Wei, D. Org. Biomol. Chem. 2019, 17, 5038–5046; https://doi.org/10.1039/c9ob00509a.Search in Google Scholar PubMed
115. Zhang, J. R., Liu, H. Y., Fan, T., Chen, Y. Y., Xu, Y. L. Adv. Synth. Catal. 2021, 363, 497–504; https://doi.org/10.1002/adsc.202000983.Search in Google Scholar
116. Belladona, A. L., Cervo, R., Alves, D., Barcellos, T., Cargnelutti, R., Schumacher, R. F. Tetrahedron Lett. 2020, 61, 152035; https://doi.org/10.1016/j.tetlet.2020.152035.Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2021-0154).
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