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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 5: 1414 - 1422

DOI: https://doi.org/10.6023/cjoc202112029

ARTICLES

Photoredox-Copper Dual-Catalyzed Site-Selective O-Alkylation of Glycosides

  • Tianyi Sun ,
  • Yifan Zhang ,
  • Yuanjie Meng ,
  • Yi Wang ,
  • Qifeng Zhu ,
  • Yuxin Jiang ,
  • Shihui Liu
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  • College of Medicine, Jiaxing University, Jiaxing, Zhejiang 314001
*Corresponding authors. E-mail: ;
;

Received date: 2021-12-22

  Revised date: 2022-01-18

  Online published: 2022-02-18

Supported by

National Natural Science Foundation of China(22001096); Natural Science Foundation of Zhejiang Province(LQ21B020008); Start up Funds of Jiaxing University(CD70519040); Jiaxing University “Hundred Youth” Training Talents(CD70621018)

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Abstract

A photoredox-copper dual-catalyzed cross dehydrogenative coupling reaction of glycosides with benzylic C—H substrates has been developed. The reaction proceeds smoothly under mild reaction conditions and features the using of readily accessible starting materials, which allows the highly site-selective synthesis of diverse glycosides O-alkylation products in 27%~72% yields, providing a new synthetic tool for the site-selective modification of glycosides.

Key words： photoredox catalysis; copper catalysis; site-selective alkylation; glycosides

Cite this article

Tianyi Sun , Yifan Zhang , Yuanjie Meng , Yi Wang , Qifeng Zhu , Yuxin Jiang , Shihui Liu . Photoredox-Copper Dual-Catalyzed Site-Selective O-Alkylation of Glycosides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1414 -1422 . DOI: 10.6023/cjoc202112029

References

[1]
(a) Seeberger, P. H.; Werz, D. B. Nature 2007, 446, 1046.
[1]
(b) Elshahawi, S. I.; Shaaban, K. A.; Kharel, M. K.; Thorson, J. S. Chem. Soc. Rev. 2015, 44, 7591.
[1]
(c) Varki, A. Glycobiology 2017, 27, 3.
[1]
(d) Wei, M.; Wang, Y.; Ye, X. Med. Res. Rev. 2018, 38, 1003.
[2]
(a) Wei, L.; Hu, F.; Chen, Z.; Shen, Y.; Zhang, L.; Min, W. Acc. Chem. Res. 2016, 49, 1494.
[2]
(b) Tiwari, V. K.; Mishra, B. B.; Mishra, K. B.; Mishra, N.; Singh, A. S.; Chen, X. Chem. Rev. 2016, 116, 3086.
[3]
(a) Dimakos, V.; Taylor, M. S. Chem. Rev. 2018, 118, 11457.
[3]
(b) Leng, W.; Yao, H.; He, J.; Liu, X. Acc. Chem. Res. 2018, 51, 628.
[3]
(c) Wang, H.; Blaszczyk, S. A.; Xiao, G.; Tang, W. Chem. Soc. Rev. 2018, 47, 681.
[3]
(d) Nielsen, M. M.; Pedersen, C. M. Chem. Rev. 2018, 118, 8285.
[3]
(e) Blaszczyk, S. A.; Homan, T.; Tang, W. Carbohydr. Res. 2019, 471, 64.
[3]
(f) Shang, W.; He, H.; Niu, D. Carbohydr. Res. 2019, 474, 16.
[3]
(g) Báti, G.; He, J.; Pal, K. B.; Liu, X. Chem. Soc. Rev. 2019, 48, 4006.
[4]
(a) Crich, D.; Vinogradova, O. J. Org. Chem. 2007, 72, 6513.
[4]
(b) Giordano, M.; Iadonisi, A. J. Org. Chem. 2014, 79, 213.
[4]
(c) Xu, H. Lu, Y.; Zhou, Y.; Ren, B.; Pei, Y.; Dong, H.; Pei, Z. Adv. Synth. Catal. 2014, 356, 1735.
[4]
(d) Saikam, V.; Dara, S.; Yadav, M.; Singh, P.; Vishwakarma, R. A. J. Org. Chem. 2015, 80, 11916.
[4]
(e) Xu, H.; Zhang, Y.; Dong, H.; Lu, Y.; Pei, Y.; Pei, Z. Tetrahedron Lett. 2017, 58, 4039.
[5]
(a) Gridley, J. J.; Osborn, H. M. I.; Suthers, W. G. Tetrahedron Lett. 1999, 40, 6991.
[5]
(b) Osborn, H. M. I.; Brome, V. A.; Harwood, L. M.; Suthers, W. G. Carbohydr. Res. 2001, 332, 157.
[5]
(c) Ren, B.; Wang, J.; Zhang, M.; Chen, Y.; Zhao, W. Adv. Synth. Catal. 2022, 364, 665.
[6]
Gangadharmath, U. B.; Demchenko, A. V. Synlett 2004, 2191.
[7]
Malik, S.; Dixit, V. A.; Bharatam, P. V.; Kartha, K. P. R. Carbohydr. Res. 2010, 345, 559.
[8]
(a) Ren, B.; Ramstro?m, O.; Zhang, Q.; Ge, J.; Dong, H. Chem.-Eur. J. 2016, 22, 2481.
[8]
(b) Ren, B.; Yan, N.; Gan, L. RSC Adv. 2017, 7, 46257.
[8]
(c) Ren, B.; Lv, J.; Zhang, Y.; Tian, J.; Dong, H. ChemCatChem 2017, 9, 950.
[9]
(a) Oshima, K.; Kitazono, E.-I.; Aoyama, Y. Tetrahedron Lett. 1997, 38, 5001.
[9]
(b) Chan, L.; Taylor, M. S. Org. Lett. 2011, 13, 3090.
[9]
(c) Dimitrijevic, E.; Taylor, M. S. Chem. Sci. 2013, 4, 3298.
[10]
(a) Li, R.-Z.; Tang, H.; Wan, L.; Zhang, X.; Fu, Z.; Liu, J.; Yang, S.; Jia, D.; Niu, D. Chem 2017, 3, 834.
[10]
(b) Li, R.-Z.; Tang, H.; Yang, K. R.; Wan, L.-Q.; Zhang, X.; Liu, J.; Fu, Z.; Niu, D. Angew. Chem., Int. Ed. 2017, 56, 7213.
[11]
(a) Li, X.; Liu, Q. Chin. J. Org. Chem. 2021, 41, 863. (in Chinese)
[11]
(李祥盛, 刘强, 有机化学, 2021, 41, 863.)
[11]
(b) Dai, P.; Xu, L. Chin. J. Org. Chem. 2021, 41, 4690. (in Chinese)
[11]
(代鹏程, 徐亮, 有机化学, 2021, 41, 4690.)
[11]
(c) Dong, K.; Liu, Q.; Wu, L.-Z. Acta Chim. Sinica 2020, 78, 299. (in Chinese)
[11]
(董奎, 刘强, 吴骊珠, 化学学报, 2020, 78, 299.)
[11]
(d) Zhang, H.-H.; Yu, S. Acta Chim. Sinica 2019, 77, 832. (in Chinese)
[11]
(张洪浩, 俞寿云, 化学学报, 2019, 77, 832.)
[12]
Dong, M.; Jia, Y.; Zhou, W.; Gao, J.; Lv, X.; Luo, F.; Zhang, Y.; Liu, S. Org. Chem. Front. 2021, 8, 6881.
[13]
(a) Lee, B. J.; DeGlopper, K. S.; Yoon, T. P. Angew. Chem., Int. Ed. 2020, 59, 197.
[13]
(b) Hu, H.; Chen, S.-J.; Mandal, M.; Pratik, S. M.; Buss, J. A.; Krska, S. W.; Cramer, C. J.; Stahl, S. S. Nat. Catal. 2020, 3, 358.
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