Citation: Zhao Zhuanxia, Wang Junjiao, Huang Danfeng, Yang Zheng, Zhao Fangxia, Hu Yongqin, Xu Weigang, Hu Yulai. Study on Tin Powder-Promoted Allylation of 3-Aryl-3-hydroxy-2-oxindoles[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 2026-2034. doi: 10.6023/cjoc202003002 shu

Study on Tin Powder-Promoted Allylation of 3-Aryl-3-hydroxy-2-oxindoles

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Huang Danfeng, huangdf@nwnu.edu.cn
Received Date: 1 March 2020
Revised Date: 9 April 2020
Available Online: 23 April 2020
Fund Project: the National Natural Science Foundation of China 21861033the National Natural Science Foundation of China 21462037the Natural Science Foundation of Gansu Province 18JR3RA091Project supported by the National Natural Science Foundation of China (Nos. 21861033, 21462037), and the Natural Science Foundation of Gansu Province (No. 18JR3RA091)

Figures(4)

An efficient tin-powder-promoted C-C coupling reaction of 3-aryl-3-hydroxy-2-oxindoles with allyl bromide was disclosed, which makes tin-powder-promoted reactions beyond 1, 2-addition to C=O or C=N double bounds, and provides a convenient and facile protocol for the synthesis of potentially bioactive 3, 3'-disubstituted-2-oxindoles in good to excellent yields. The method is highly efficient and environmentally benign with low cost and concise manipulation.
- tin powder,
- 3-hydroxy-2-oxindoles,
- allylation,
1. [1]
  (a) Roy, U. K.; Roy, S. Chem. Rev. 2010, 110, 2472.
  (b) Zha, Z.; Hui, A.; Zhou, Y.; Miao, Q.; Wang, Z.; Zhang, H. Org. Lett. 2005, 7, 1903.
  (c) Crich, D.; Grant, D.; Krishnamurthy, V.; Patel, M. Acc. Chem. Res. 2007, 40, 453.
  (d) Davies, A. G.; Gielen, M.; Pannell, K. H.; Tiekink, E. R. T. Tin chemistry: Fundamentals, Frontiers, and Applications; John Wiley & Sons, Chichester, U.K., 2008.
2. [2]
  (a) Hoch, M. Appl. Geochem. 2001, 16, 719.
  (b) Amouroux, D.; Tessier, E.; Donard, O. F. X. Environ. Sci. Technol. 2000, 34, 988.
  (c) Lukevics, E.; Pudova, O. Biological Activity of Organotin and Organolead Compounds. In the Chemistry of Organic Germanium, Tin and Lead Compounds, Vol. 2, Ed.: Rappoport, Z., John Wiley and Sons, Chichester, 2002, p. 1685.
  (d) Barnes, J. M.; Stoner, H. B. Pharmacol. Rev. 1959, 11, 211.
3. [3]
  (a) Solin, N.; Kjellgren, J.; Szabó, K. J. J. Am. Chem. Soc. 2004, 126, 7026.
  (b) Teo, Y.-C.; Goh, J.-D.; Loh, T.-P. Org. Lett. 2005, 7, 2743.
  (c) Suzuki, T.; Atsumi, J.-I.; Sengoku, T.; Takahashi, M.; Yoda, H. J. Organomet. Chem. 2010, 695, 128.
  (d) Deng, D.; Liu, P.; Ji, B.; Wang, L.; Fu, W. Tetrahedron Lett. 2010, 51, 5567.
  (e) Cormier, M.; Ahmad, M.; Maddaluno, J.; Paolis, M. D. Organometallics 2017, 36, 4920.
  (f) Mahajani, N. S.; Chisholm, J. D. Org. Biomol. Chem. 2018, 16, 4008.
4. [4]
  Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 10, 1527. doi: 10.1246/cl.1981.1527
5. [5]
  (a) Elaas, N. A.; Elaas, W. A.; Huang, D.; Hu, Y.; Wang, K.-H. Curr. Org. Synth. 2017, 14, 1156.
  (b) Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958.
  (c) Alcaide, B.; Almendros, P.; Rodríguez-Acebes, R. J. Org. Chem. 2005, 70, 2713.
  (d) Appelt, H. R.; Limberger, J. B.; Weber, M.; Rodrigues, O. E. D.; Oliveira, J. S.; Lüdtke, D. S.; Braga, A. L. Tetrahedron Lett. 2008, 49, 4956.
  (e) Thorat, P. B.; Goswami, S. V.; Bhusare, S. R. Tetrahedron: Asymmetry 2013, 24, 1324.
  (f) Wang, Z.; Zha, Z.; Zhou, C. Org. Lett. 2002, 4, 1683.
  (g) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208.
  (h) Estevam, I. H. S.; Bieber, L. W. Tetrahedron Lett. 2003, 44, 667
6. [6]
  (a) Lin, M.-H.; Lin, L.-Z.; Chuang, T.-H.; Liu, H.-J. Tetrahedron 2012, 68, 2630.
  (b) Lin, M.-H.; Hung, S.-F.; Lin, L.-Z.; Tsai, W.-S.; Chuang, T.-H. Org. Lett. 2011, 13, 332.
  (c) Lin, M.-H.; Lin, W.-C.; Liu, H.-J.; Chuang, T.-H. J. Org. Chem. 2013, 78, 1278.
7. [7]
  Liao, P.-H.; Bao, W.-L.; Zhang, Y.-M. Synth. Chem. 1997, 5, 374.
8. [8]
9. [9]
  (a) Naredla, R. R.; Klumpp, D. A. Chem. Rev. 2013, 113, 6905.
  (b) Nokami, T.; Yamane, Y.; Oshitani, S.; Kobayashi, J.-K, Matsui, S.-i.; Nishihara, T.; Uno, H.; Hayase, S.; Itoh, T. Org. Lett. 2015, 17, 3182.
  (c) Flagstad, T.; Petersen, M. T.; Nielsen, T. E. Angew. Chem., Int. Ed. 2015, 54, 8395.
  (d) Xiao, M.; Ren, D, Xu, L.; Li, S.-S.; Yu, L.; Xiao, J. Org. Lett. 2017, 19, 5724.
  (e) Hikawa, H.; Kotaki, F.; Kikkawa, S.; Azumaya, I. J. Org. Chem. 2019, 84, 1972.
  (f) Yu, H.; Lee, R.; Kim, H.; Lee, D. J. Org. Chem. 2019, 84, 3566.
  (g) Mayer, R. J.; Breugst, M.; Hampel, N.; Ofial, A. R.; Mayr, H. J. Org. Chem. 2019, 84, 8837.
  (h) Kinthada, L. K.; Medisetty, S. R.; Parida, A.; Babu, K. N.; Bisai, A. J. Org. Chem. 2017, 82, 8548.
10. [10]
  Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452. doi: 10.1021/jo9901337
11. [11]
  Lebleu, T.; Paquin, J-F. Tetrahedron Lett. 2017, 58, 442. doi: 10.1016/j.tetlet.2016.12.056
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