Citation: Sui Jing-Jing, Xiong De-Cai, Ye Xin-Shan. Copper-mediated O-arylation of lactols with aryl boronic acids[J]. Chinese Chemical Letters, ;2019, 30(8): 1533-1537. doi: 10.1016/j.cclet.2019.06.014 shu

Copper-mediated O-arylation of lactols with aryl boronic acids

Sui Jing-Jing ^a,b ,
Xiong De-Cai ^b,c,*, ,
Ye Xin-Shan ^a,b,*,

a.
National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China
b.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
c.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

decai@bjmu.edu.cn

xinshan@bjmu.edu.cn

Received Date: 7 May 2019
Revised Date: 3 June 2019
Accepted Date: 6 June 2019
Available Online: 8 August 2019

Figures(2)

An efficient and novel methodology to access phenolic glycosides has been established by using coppermediated coupling reaction of aryl boronic acids with hemiacetals. The reaction takes place normally in the presence of Cu(OAc)₂ (1.0 equiv.) and pyridine (2.0 equiv.) at 40℃. This protocol distinguishes itself by wide substrate scope, operational simplicity and giving rise to a myriad of phenolic glycosides in good to excellent yields.
- Phenolic glycoside,
- O-Arylation,
- Lactol,
- Aryl boronic acid
1. [1]
  D. Kahne, C. Leimkuhler, L. Wei, et al., Chem. Rev. 105(2005) 425-448. doi: 10.1021/cr030103a
2. [2]
  S.Y. Lee, W. Kim, Y.G. Lee, et al., Pharmacol. Res. 119(2017) 422-430. doi: 10.1016/j.phrs.2017.03.003
3. [3]
  W. Li, R.J. Dai, Y.H. Yu, et al., Biol. Pharm. Bull. 30(2007) 1123-1129. doi: 10.1248/bpb.30.1123
4. [4]
  (a) R. Riccio, K. Nakanishi, J. Org. Chem. 47 (1982) 4589-4592;
  (b) B. La Ferla, C. Airoldi, C. Zona, et al., Nat. Prod. Rep. 28 (2011) 630-648;
  (c) C. Mendez, J. Gonzalez-Sabin, F. Moris, et al., Planta Med. 81 (2015) 1326-1338;
  (d) H. Murase, T. Noguchi, S. Sasaki, Bioorg. Med. Chem. Lett. 28 (2018) 1832-1835;
  (e) B.T. Scroggins, J. Burkeen, A.O. White, et al., Int. J. Radiat. Oncol. Biol. Phys. 100 (2018) 344-352;
  (f) N. Tatematsu, Y. Waguri-Nagaya, Y. Kawaguchi, et al., Mod. Rheumatol. 28 (2018) 495-505.
5. [5]
  (a) S. Burda, W. Oleszek, J. Agric. Food Chem. 49 (2001) 2774-2779;
  (b) Y.S.R. Elnaggar, E.M.M. Shehata, S. Galal, Nanomedicine 12 (2017) 893-910.
6. [6]
  C.S. Kim, L. Subedi, K.J. Park, et al., Fitoterapia 106(2015) 147-152. doi: 10.1016/j.fitote.2015.08.013
7. [7]
  (a) W. Koenigs, E. Knorr, Ber. Dtsch. Chem. Ges. 34 (1901) 957-981;
  (b) K. Mohri, Y. Watanabe, Y. Yoshida, et al., Chem. Pharm. Bull. 51 (2003) 1268-1272.
8. [8]
  (a) R.R. Schmidt, J. Miche, Angew. Chem. Int. Ed. 19 (1980) 731-732;
  (b) D.A. Burnett, M.A. Caplen, M.S. Domalski, et al., Bioorg. Med. Chem. Lett. 12 (2002) 311-314;
  (c) P.W. Qin, J. Wang, H. Wang, et al., J. Agric. Food Chem. 62 (2014) 4521-4527.
9. [9]
  (a) M. Li, X.W. Han, B. Yu, J. Org. Chem. 68 (2003) 6842-6845;
  (b) C. Menozzi-Smarrito, C.C. Wong, W. Meinl, et al., J. Agric. Food Chem. 59 (2011) 5671-5676.
10. [10]
  Y.S. Lee, E.S. Rho, Y.K. Min, et al., J. Carbohydr. Chem. 20(2001) 503-506. doi: 10.1081/CAR-100106933
11. [11]
  (a) S.G. Duron, T. Polat, C.H. Wong, Org. Lett. 6 (2004) 839-841;
  (b) G.J. Liu, C.Y. Li, X.T. Zhang, et al., Chin. Chem. Lett. 29 (2018) 1-10.
12. [12]
  (a) Y. Hu, Y.H. Tu, D.Y. Liu, et al., Org. Biomol. Chem. 14 (2016) 4842-4847;
  (b) J.F. Zhou, X. Chen, Q.B. Wang, et al., Chin. Chem. Lett. 21 (2010) 922-926.
13. [13]
  C.F. Liu, D.C. Xiong, X.S. Ye, Tetrahedron Lett. 57(2016) 1372-1374. doi: 10.1016/j.tetlet.2016.02.059
14. [14]
  (a) W.R. Roush, R.A. Hartz, D.J. Gustin, J. Am. Chem. Soc.121 (1999) 1990-1991;
  (b) L. Petersen, K.J. Jensen, J. Org. Chem. 66 (2001) 6268-6275;
  (c) J.P. Issa, C.S. Bennett, J. Am. Chem. Soc. 136 (2014) 5740-5744.
15. [15]
  (a) G.L. Tolnai, U.J. Nilsson, B. Olofsson, Angew. Chem. Int. Ed. 55 (2016) 11226[-11230;
  (b) N. Lucchetti, R. Gilmour, Chem. -Eur. J. 24 (2018) 16266-16270.
16. [16]
  H. Ye, C. Xiao, Q.Q. Zhou, et al., J. Org. Chem. 83(2018) 13325-13334. doi: 10.1021/acs.joc.8b02129
17. [17]
  (a) D.C. Xiong, L.H. Zhang, X.S. Ye, Org. Lett. 11 (2009) 1709-1712;
  (b) C.F. Liu, D.C. Xiong, X.S. Ye, J. Org. Chem. 79 (2014) 4676-4686;
  (c) S.B. Tang, Q.N. Zheng, D.C. Xiong, et al., Org. Lett. 20 (2018) 3079-3082.
18. [18]
  (a) S.V. Ley, A.W. Thomas, Angew. Chem. Int. Ed. 42 (2003) 5400-5449;
  (b) A.E. King, T.C. Brunold, S.S. Stahl, J. Am. Chem. Soc. 131 (2009) 5044-5045.
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