Citation: Zhang Shuo, Peng Dan, Zhao Ning, Yu Yitao, Wang Feng, Liu Hailong, Yi Gang. Sc(OTf)₃ Catalyzed Oxo-Michael Addition to o-Quinone Methides by Alcohols[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 555-560. doi: 10.6023/cjoc201807017 shu

Sc(OTf)₃ Catalyzed Oxo-Michael Addition to o-Quinone Methides by Alcohols

Zhang Shuo ^a ,
Peng Dan ^a ,
Zhao Ning ^a ,
Yu Yitao ^a ,
Wang Feng ^a ,
Liu Hailong ^b ,
Yi Gang ^b,,

a.
Shandong Provincial Key Laboratory for Special Silicone-Containing Materials, Advanced Materials Institute, Qilu University of Technology(Shandong Academy of Sciences), Jinan 250014
b.
Shandong Dongyue Organosilicon Materials Co., Ltd., Zibo 256401

Corresponding author: Yi Gang, yigang009@163.com
Received Date: 9 July 2018
Revised Date: 26 August 2018
Available Online: 10 February 2018
Fund Project: the National Natural Science Foundation of China 51503118Project supported by the Shandong Provincial Natural Science Foundation (No. ZR2017BB033), the Youth Science Funds of Shandong Academy of Sciences (No. 2018QN0030) and the National Natural Science Foundation of China (No. 51503118)the Shandong Provincial Natural Science Foundation ZR2017BB033the Youth Science Funds of Shandong Academy of Sciences 2018QN0030

Figures(4)

o-Quinone derivatives are not only a variety of active and important intermediate, but also widely used in the synthesis of natural products and medicinal chemistry. In the present study, the Sc(OTf)₃ catalyzed oxo-Michael addition to o-quinone methides by alcohols was developed. The products were obtained in moderate to good yields (76%~97%) under mild conditions. Furthermore, the reaction could be scaled up to multigram scale.
- o-quinone,
- scandium(Ⅲ) triflate,
- oxo-Michael addition,
- green chemistry
1. [1]
  Pathak, T. P.; Sigman, M. S. J. Org. Chem. 2011, 76, 9210. doi: 10.1021/jo201789k
2. [2]
  Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18, 9160. doi: 10.1002/chem.v18.30
3. [3]
  Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733. doi: 10.3390/molecules200711733
4. [4]
  Wang, Z.; Sun, J. Synthesis 2015, 47, 3629. doi: 10.1055/s-00000084
5. [5]
  Guo, C.; Song, J.; Luo, S.; Gong, L. Z. Angew. Chem., Int. Ed., 2010, 49, 5558. doi: 10.1002/anie.201002108
6. [6]
  Van De Water, R, W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367. doi: 10.1016/S0040-4020(02)00496-9
7. [7]
  Kulikov, A.; Arumugam, S.; Popik, V. V. J. Org. Chem. 2008, 73, 7611. doi: 10.1021/jo801302m
8. [8]
  Mattson, A. E.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 4508. doi: 10.1021/ja068189n
9. [9]
  Luan, Y.; Schaus, S. E. J. Am. Chem. Soc. 2012, 134, 19965. doi: 10.1021/ja309076g
10. [10]
  Shaikh, A. K.; Cobb, A. J. A.; Varounis, G. Org. Lett. 2012, 14, 584. doi: 10.1021/ol203196n
11. [11]
  Chen, M. W.; Gao, L. L.; Ye, Z. S.; Jiang, G. F.; Zhou, Y. G. Chem. Commun. 2013, 49, 1660. doi: 10.1039/c3cc37800d
12. [12]
  Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. A. Org. Lett. 2004, 6, 4049. doi: 10.1021/ol048298b
13. [13]
  Bai, W. J.; David, J. G.; Feng, Z. G.; Weaver, M. G.; Wu, K. L.; Pettus, T. R. R. Acc. Chem. Res. 2014, 47, 3655. doi: 10.1021/ar500330x
14. [14]
  Caruana, L.; Fochi, M.; Bernardi, L. Molecules 2015, 20, 11733. doi: 10.3390/molecules200711733
15. [15]
  Wang, Z.; Sun, J. Synthesis 2015, 47, 3629. doi: 10.1055/s-00000084
16. [16]
  Zhao, W.; Wang, Z.; Chu, B.; Sun, J. Angew. Chem., Int. Ed. 2015, 54, 1910. doi: 10.1002/anie.201405252
17. [17]
  Huang, Y.; Hayashi, T. J. Am. Chem. Soc. 2015, 137, 7556. doi: 10.1021/jacs.5b03277
18. [18]
  Wang, Z.; Ai, F.; Wang, Z.; Zhao, W.; Zhu, G.; Lin, Z.; Sun, J. J. Am. Chem. Soc. 2015, 137, 383. doi: 10.1021/ja510980d
19. [19]
  Wu, B.; Yu, Z.; Gao, X.; Lan, Y.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2017, 56, 4006. doi: 10.1002/anie.201700437
20. [20]
  Chen, P.; Wang, K. l; Guo, W.; Liu, X.; Liu, Y.; Li, C. Angew. Chem., Int. Ed. 2017, 56, 3689. doi: 10.1002/anie.201700250
21. [21]
  Nising, C. F.; Brase, S. Chem. Soc. Rev. 2008, 37, 1218. doi: 10.1039/b718357g
22. [22]
  Nising, C. F.; Brase, S. ̈Chem. Soc. Rev. 2012, 41, 988. doi: 10.1039/C1CS15167C
23. [23]
  Heravi, M. M.; Hajiabbasi, P. Mol. Diversity 2014, 18, 411. doi: 10.1007/s11030-013-9494-2
24. [24]
  Gu, Q.; Rong, Z.-Q.; Zheng, C.; You, S. L. J. Am. Chem. Soc. 2010, 132, 4056. doi: 10.1021/ja100207s
25. [25]
  Rubush, D. M.; Morges, M. A.; Rose, B. J.; Thamm, D. H.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 13554. doi: 10.1021/ja3052427
26. [26]
  Shi, Y. L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499. doi: 10.1039/B618984A
27. [27]
  Liang, M.; Zhang, S.; Jia, J.; Tung, C.-H.; Wang, J. W.; Xu, Z. H. Org. Lett. 2017, 19, 2526. doi: 10.1021/acs.orglett.7b00804
28. [28]
  Lai, Z. W.; Wang, Z. B.; Sun, J. W. Org. Lett. 2015, 17, 6058. doi: 10.1021/acs.orglett.5b03072
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Sc(OTf)3 Catalyzed Oxo-Michael Addition to o-Quinone Methides by Alcohols

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Sc(OTf)₃ Catalyzed Oxo-Michael Addition to o-Quinone Methides by Alcohols