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Recent Progress on Alkyl-, Aryl- and Fluoroalkyl-selenylation Reactions

  • Shan Li ,
  • Yuan Cao ,
  • Lüqi Jiang
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  • a Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094
    b Shazhou Professional Institute of Technology, Zhangjiagang, Jiangsu 215600
These authors contributed equally to this work.

Received date: 2021-08-02

  Revised date: 2021-09-23

  Online published: 2021-10-15

Supported by

National Natural Science Foundation of China(21776138); National Natural Science Foundation of China(22078161); National Natural Science Foundation of China(22108124); Fundamental Research Funds for the Central Universities(30918011314); Natural Science Foundation of Jiangsu Province(BK20141394); Qing Lan and Six Talent Peaks in Jiangsu Province(22108124)

Abstract

Organoselenium compounds have great application value in the fields of medicine, pesticide, synthesis and materials, and play a particularly prominent role in anti-cancer and anti-inflammatory. Therefore, the synthesis of organoselenium compounds is particularly important in organic synthesis. The traditional methods of synthesizing organoselenium compounds were using selenol or selenium ether react with alkylation or arylation reagents. Various direct alkyl- and aryl-selenylation reagents were also developed in recent years. Moreover, there are few studies on fluoroalkylselenylation. Thus, it is still highly desirable to develop new methods for alkyl-, aryl- and fluoro-alkylselenylation as well as new types of corresponding selenylation reagents. The recent development of alkyl-, aryl- and fluoro-alkylselenylation is summarized, and part of their mechanisms are also discussed.

Cite this article

Shan Li , Yuan Cao , Lüqi Jiang . Recent Progress on Alkyl-, Aryl- and Fluoroalkyl-selenylation Reactions[J]. Chinese Journal of Organic Chemistry, 2022 , 42(2) : 434 -457 . DOI: 10.6023/cjoc202108001

References

[1]
Shen, L. Q. Chem. World 2009, 50, 511. (in Chinese)
[1]
( 申兰芹, 化学世界, 2009, 50, 511.)
[2]
Chen, H. Z. Internal Medicine, People’s Medical Publishing House Co., Ltd, Peking, 1989, pp. 299-300. (in Chinese)
[2]
( 陈灏珠, 内科学, 人民卫生出版社, 北京, 1989, pp. 299-300.)
[3]
Chen, X. Q.; Jin, Y. Y.; Tang, G. New Pharmacology, People’s Medical Publishing House Co., Ltd, Peking, 2005, p. 776. (in Chinese)
[3]
( 陈新谦, 金有豫, 汤光, 新编药物学, 人民卫生出版社, 北京, 2005, p. 776.)
[4]
Kryukov, G. V.; Castellano, S.; Novoselov, S. V.; Lobanov, A. V.; Zehtab, O.; Guigó, R.; Gladyshev, V. N. Science 2003, 300, 1439.
[5]
Allmang, C.; Wurth, L. Biochim. Biophys. Acta 2009, 1790, 1415.
[6]
Schewe, C.; Schewe, T.; Wendel, A. Biochem. Pharmacol. 1994, 48, 65.
[7]
Tiano, L.; Fedeli, D.; Santoni, G.; Davies, I.; Wakabayashi, T.; Falcioni, G. Mitochondrion 2003, 2, 428.
[8]
Rossato, J. I.; Zen, G.; Mello, C. F.; Rubin, M. A.; Rocha, J. B. Neurosci. Lett. 2002, 318, 137.
[9]
Meotti, F. C.; Stangherlin, E. C.; Zeni, G.; Nogueira, C. W.; Rocha, J. B. Environ. Res. 2004, 94, 276.
[10]
Rossato, J. I.; Ketzer, L. A.; Centuriao, F. B.; Silva, S. J.; Ludtke, D. S.; Zeni, G.; Braga, A. L.; Rubin, M. A.; Rocha, J. B. Neurochem. Res. 2002, 27, 297.
[11]
Nogueira, C. W.; Zeni, G.; Rocha, J. B. Chem. Rev. 2004, 104, 6255.
[12]
Zhang, S.; An, B. J.; Li, J. Y.; Hu, J. H.; Huang, L.; Li, X. S.; Chan, S. C. Org. Biomol. Chem. 2017, 15, 7404.
[13]
Ip, C.; Ganther, H. E. Carcinogenesis 1992, 13, 1167.
[14]
Zeng, H.; Cheng, W. H.; Johnson, L. K. J. Nutr. Biochem. 2013, 24, 776.
[15]
Lin, T.; Ding, Z.; Li, N.; Xu, J.; Luo, G.; Liu, J.; Shen, J. Eur. J. Cancer 2011, 47, 1890.
[16]
Ganther, H. E.; Ip, C. J. Nutr. 2001, 131, 301.
[17]
Wendel, A.; Tiegs, G. Biochem. Pharmacol. 1986, 35, 2115.
[18]
Tabuchi, Y.; Kurebayashi, Y. Jpn. J. Pharmacol. 1993, 61, 255.
[19]
Beil, W.; Staar, U.; Sewing, K. F. Biochem. Pharmacol. 1990, 40, 1997.
[20]
Yamaguchi, T.; Sano, K.; Takakura, K.; Saito, I.; Shinohara, Y.; Asano, T.; Yasuhara, H. Stroke 1998, 29, 12.
[21]
Sohn, O. S.; Blackwell, L.; Mathis, J.; Asaad, W. W.; Reddy, B. S.; El-Bayoumy, K. Drug Metab. Dispos. 1991, 19, 865.
[22]
Guan, Q.; Han, C. M.; Zuo, D. Y.; Zhai, M. A.; Li, Z. Q.; Zhang, Q.; Zhai, Y. P.; Jiang, X. W.; Bao, K.; Wu, Y. L.; Zhang, W. G. Eur. J. Med. Chem. 2014, 87, 306.
[23]
Wen, Z.; Xu, J.; Wang, Z.; Qi, H.; Bai, Z.; Zhang, Q.; Bao, K.; Wu, Y.; Zhang, W. Eur. J. Med. Chem. 2015, 90, 184.
[24]
Ali, H.; van Lier, J. E. J. Chem. Soc., Perkin Trans. 1 1991, 269.
[25]
Engman, L.; Stern, D.; Frisell, H.; Vessman, K.; Berglund, M.; Ek, B.; Andersson, C. M. Bioorg. Med. Chem. 1995, 3, 1255.
[26]
Casaril, A. M.; Ignasiak, M. T.; Chuang, C. Y.; Vieira, B.; Padilha, N. B.; Carroll, L.; Lenardao, E. J.; Savegnago, L.; Davies, M. J. Free Radicals Biol. Med. 2017, 113, 395.
[27]
Kumar, S.; Sharma, N.; Maurya, I. K.; Bhasin, A. K. K.; Wangoo, N.; Brandao, P.; Fleix, V.; Bhasin, K. K.; Kumar, R. K. Eur. J. Med. Chem. 2016, 123, 916.
[28]
Nakatsubo, N.; Kojima, H.; Sakurai, K. Biol. Pharm. Bull. 1998, 21, 1247.
[29]
Yan, J.; Pang, Y. Q.; Zhuang, J. L.; Lin, H. B.; Zhang, X.; Han, L. Q.; Ke, P. F.; Zhuang, J. H.; Huang, X. Z. ACS Chem. Neurosci. 2019, 10, 2903.
[30]
He, X. R.; Yang, R. CN 110041342, 2019.
[31]
Zhang, P.; Lu, L.; Shen, Q. Acta Chim. Sinica 2017, 75, 744. (in Chinese)
[31]
( 张盼盼, 吕龙, 沈其龙, 化学学报, 2017, 75, 744.)
[32]
Zhang, K.; Xu, X.-H.; Qing, F.-L. Chin. J. Org. Chem. 2015, 35, 556. (in Chinese)
[32]
( 张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.)
[33]
Rossi, A. R.; Pefibfiory. A. B. J. Org. Chem. 1981, 46, 4580.
[34]
Gladysz, J. A.; Hornby, J. L.; Garbe, J. E. J. Org. Chem. 1978, 43, 1204.
[35]
Hartke, K.; Wendebourg, H. H. Heterocycles 1988, 27, 639.
[36]
Barton, D. H. R.; Finet, J.; Thmas, M. Tetrahedron 1988, 44, 6397.
[37]
Iwasaki, M.; Tsuchiya, Y.; Nakajima, K.; Nishihara, Y. Org. Lett. 2014, 16, 4920.
[38]
Ferreira, N. L.; Azeredo, J. B.; Fiorentin, B. L.; Braga, A. L. Eur. J. Org. Chem. 2015, 2015, 5070.
[39]
Santos, K. S.; Sandagorda, E. M. A.; Cargnelutti, R.; Barcellos, T.; Jacob, R. G.; Alves, D.; Schumacher, R. F. ChemistrySelect 2017, 2, 10793.
[40]
Wang, J.; Li, H.; Leng, T.; Liu, M.; Ding, J.; Huang, X.; Wu, H.; Gao W.; Wu. G. Org. Biomol. Chem. 2017, 15, 9718
[41]
Yu, J. M.; Cai, C. Org. Biomol. Chem. 2018, 16, 490.
[42]
Saba, S.; Rafique, J.; Franco, M. S.; Schneider, A. R.; Espíndola, L.; Silva, D. O.; Braga, A. Org. Biomol. Chem. 2018, 16, 880.
[43]
Liu, M. X.; Li, Y. M.; Yu, L.; Xu, Q.; Jiang, X. F. Sci. China Chem. 2018, 61, 294.
[44]
Wang, X.; Li, N.; Wang, H.; Liu, W.; Diao, H.; Xu, X. Chin. J. Org. Chem. 2019, 39, 1802. (in Chinese)
[44]
( 王灵晓, 李宁波, 王浩江, 刘文, 刁海鹏, 许新华, 有机化学, 2019, 39, 1802.)
[45]
Wang, L. X.; Qiao, J.; Wei, J. C.; Liang, Z. W.; Xu, X. H.; Li, N. B. Tetrahedron 2020, 76, 130750.
[46]
Yi, R.; Liu, S.; Gao, H.; Liang, Z. Xu, X.; Li, N. Tetrahedron 2020, 76, 130951.
[47]
Li, N.; Xu, L.; Ma, R.; Fan, Q.; Li, B.; Qiao, J.; Guo, R.; Xu, X. Chin. J. Org. Chem. 2021, 41, 2723. (in Chinese)
[47]
( 李宁波, 续立, 马榕, 范琪, 李波, 乔洁, 郭睿, 许新华, 有机化学, 2021, 41, 2723.)
[48]
Chen, J.; Wu, H.; Gui, Q.; Yan, S.; Deng, J.; Lin, Y.; Cao, Z.; He, W. Chin. J. Catal. 2021, 42, 1445.
[49]
Chen, J.; Zhong, C.; Gui, Q.; Zhou, Y.; Fang, Y.; Liu, K.; Lin, Y.; Cao, Z.; He W. Chin. Chem. Lett. 2021, 32, 475.
[50]
Wu, Y.; Chen, J.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He W. Green Chem. 2021, 23, 3950.
[51]
Min, L; Wu, G.; Liu, M.; Gao, W.; Ding, J.; Chen, J.; Huang. X.; Wu, H. J. Org. Chem. 2016, 81, 7584.
[52]
Luo, D.; Wu, G.; Yang, H.; Liu, M.; Gao, W.; Huang, X.; Chen, J.; Wu, H. J. Org. Chem. 2016, 81, 4485.
[53]
Gao, C.; Wu, G.; Min, L.; Liu, M.; Gao, W.; Ding, J.; Chen, J.; Huang, X.; Wu, H. J. Org. Chem. 2017, 82, 250.
[54]
Zhu, J.; Zhu, W.; Xie, P.; Jr Pittman, C. U.; Zhou, A. Tetrahedron 2018, 74, 6569.
[55]
Guo, T.; Wei, X. N.; Zhu, Y. L.; Chen, H.; Han, S. L.; Ma, Y. C. Synlett 2018, 29, 1530.
[56]
Guo, T.; Wei, X. N.; Liu, Y.; Zhang, P. K.; Zhao, Y. H. Org. Chem. Front. 2019, 6, 1414.
[57]
Jin, G. Q.; Gao, W. X.; Zhou, Y. B.; Liu, M. C.; Wu, H. Y. RSC Adv. 2020, 10, 30439.
[58]
Li, Y.; Wang, Y.; Yang, T.; Lin, Z.; Jiang, X. Green Chem. 2021, 23, 2986.
[59]
Zimmermann, E. G.; Thurow, S.; Freitas, C. S.; Mendes, S. R.; Perin, G.; Alves, D.; Jacob, R. G.; Lenardão, E. J. Molecules 2013, 18, 4081.
[60]
Wang, J.; Li, H.; Mei, Y. J.; Lou, B.; Xu, D. G.; Xie, D. Q.; Guo, H.; Wang, W. J. Org. Chem. 2005, 70, 5678.
[61]
Tingoli, M.; Diana, R.; Panunzi, B. Tetrahedron Lett. 2006, 47, 7529.
[62]
Denmark, S. E.; Collins, W. R. Org. Lett. 2007, 9, 3801.
[63]
Zhang, H.; Lin, S.; Jacobsen, E. N. J. Am. Chem. Soc. 2014, 136, 16485.
[64]
See, J. Y.; Yang, H.; Zhao, Y.; Wong, M. W.; Ke, Z. H.; Yeung, Y. Y. ACS Catal. 2018, 8, 850.
[65]
Movassagh, B.; Takallou, A. Synlett 2015, 2247.
[66]
Liu, F. M.; Yi, W. B. Org. Chem. Front. 2018, 5, 428.
[67]
Cao, Y.; Liu, J.; Jiang, L. Q.; Yi, W. B. Org. Chem. Front. 2019, 6, 825.
[68]
Mehta, V. P.; Greaney, M. F. Org. Lett. 2013, 15, 5036.
[69]
Heine, N. B.; Studer, A. Org. Lett. 2017, 19, 4150.
[70]
Suzuki, H.; Yoshinaga, M.; Takaoka, K.; Hiroi, Y. Synthesis 1985, 497.
[71]
Blond, G.; Billard, T.; Langlois, B. R. Tetrahedron Lett. 2001, 42, 2473.
[72]
Pooput, C.; Jr. Dolbier, W. R.; Médebielle, M. J. Org. Chem. 2006, 71, 3564.
[73]
Lin, Y. M.; Yi, W. B.; Shen, W. Z.; Lu, G. P. Org. Lett. 2016, 18, 592.
[74]
Carbonnel, E.; Besset, T.; Poisson, T.; Labar, D.; Pannecoucke, X.; Jubault, P. Chem. Commun. 2017, 53, 5706.
[75]
Nozawa-Kumada, K.; Osawa, S.; Ojima, T.; Noguchi, K.; Shigeno, M.; Kondo, Y. Asian J. Org. Chem. 2020, 9, 765.
[76]
Chen, C.; Ouyang, L.; Lin, Q.; Liu, Y.; Hou, C.; Yuan, Y.; Weng, Z. Chem. Eur. J. 2014, 20, 657.
[77]
Wang, J.; Zhang, M.; Weng, Z. J. Fluorine Chem. 2017, 193, 24.
[78]
Yang, Y.; Lin, X.; Zheng, Z.; Lin, G.; Zhang, Y.; You, Y.; Weng, Z. J. Fluorine Chem. 2017, 204, 1.
[79]
Tian, Q.; Weng, Z. Chin. J. Chem. 2016, 34, 505.
[80]
Rong, M.; Huang, R.; You, Y.; Weng, Z. Tetrahedron 2014, 70, 8872.
[81]
Wang, Y.; You, Y.; Weng, Z. Org. Chem. Front. 2015, 2, 574.
[82]
Hou, C.; Lin, X.; Huang, Y.; Chen, Z.; Weng, Z. Synthesis 2015, 47, 969.
[83]
Zhang, Y.; Yang, D.; Weng, Z. Tetrahedron 2017, 73, 3853.
[84]
Chen, T.; You, Y.; Weng, Z. J. Fluorine Chem. 2018, 216, 43.
[85]
Zhang, M.; Weng, Z. Org. Lett. 2019, 21, 5838
[86]
Chen, C.; Hou, C.; Wang, Y.; Andy Hor, T. S.; Weng, Z. Org. Lett. 2014, 16, 524.
[87]
Dong, J.; Li, Z.; Weng, Z. Org. Biomol. Chem. 2018, 16, 9269.
[88]
Geri, J. B.; Wade Wolfe, M. M.; Szymczak, N. K. Angew. Chem., Int. Ed. 2018, 57, 1381.
[89]
Chen, X. L.; Zhou, S. H.; Lin, J. H.; Deng, Q. H; Xiao, J. C. Chem. Commun. 2019, 55, 1410.
[90]
Glenadel, Q.; Ismalaj, E.; Billard, T. J. Org. Chem. 2016, 81, 8268.
[91]
Ghiazza, C.; Billard, T.; Tlili, A. Chem. Eur. J. 2017, 23, 10013.
[92]
Aufiero, M.; Sperger, T.; Tsang, A. S. K.; Schoenebeck, F. Angew. Chem., Int. Ed. 2015, 54, 10322.
[93]
Dürr, A. B.; Fisher, H. C.; Kalvet, I.; Truong, K. N.; Schoenebeck, F. Angew. Chem., Int. Ed. 2017, 56, 13431.
[94]
Lefebvre, Q.; Pluta, R.; Rueping, M. Chem. Commun. 2015, 51, 4394.
[95]
Han, J. B.; Dong, T.; Vicic, D. A.; Zhang, C. P. Org. Lett. 2017, 19, 3919.
[96]
Han, Q. Y.; Zhao, C. L.; Dong, T.; Shi, J.; Tana, K. L.; Zhang, C. P. Org. Chem. Front. 2019, 6, 2732.
[97]
Han, Q. Y.; Tan, K. L.; Wang, H. N.; Zhang, C. P. Org. Lett. 2019, 21, 10013.
[98]
Modak, A.; Pinter, E. N.; Cook, S. P. J. Am. Chem. Soc. 2019, 141, 18405.
[99]
Glenadel, Q.; Ghiazza, C.; Tlili, A.; Billard, T. Adv. Synth. Catal. 2017, 359, 3414.
[100]
Zhao, X.; Wei, X.; Tian, M.; Zheng, X.; Ji, L.; Li, Q.; Lin, Y.; Lu, K. Tetrahedron Lett. 2019, 60, 1796.
[101]
Lu, K.; Li, Q.; Xi, X.; Zhou, T.; Zhao, X. J. Org. Chem. 2020, 85, 1224.
[102]
Dix, S.; Jakob, M.; Hopkinson, M. N. Chem. Eur. J. 2019, 25, 7635.
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