Citation: Jiang Xiaoli, Dai Wei, Zhao Jiajia, Shi Feng. Brønsted Acid Catalyzed Reaction of ortho-Hydroxylstyrenes with Indoles: Synthesis of 1,1-Diarylethanes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 1014-1020. doi: 10.6023/cjoc201601002 shu

Brønsted Acid Catalyzed Reaction of ortho-Hydroxylstyrenes with Indoles: Synthesis of 1,1-Diarylethanes

1.
School of Chemistry & Chemical Engineering, Jiangsu Normal University, Xuzhou 221116

Corresponding author: Shi Feng, fshi@jsnu.edu.cn
Received Date: 2 January 2016
Revised Date: 26 January 2016

Fund Project: Project supported by the National Natural Science Foundation of China No. 21372002

Figures(2)

The skeleton of 1,1-diarylethane exists in many biologically important molecules. So, the synthesis of 1,1-diarylethanes has absorbed great attention from the chemists. This work has established a reaction of ortho-hydroxylstyrenes with indoles in the presence of racemic phosphoric acid, leading to the efficient synthesis of a series of 1,1-diarylethanes with structural diversity in high yields (up to 99%). This reaction is based on the fact that ortho-hydroxylstyrenes could transform into ortho-quinone methide under the catalysis of racemic phosphoric acid. The dual activation mode of racemic phosphoric acid to ortho-quinone methide and indole via forming two hydrogen bonds contributed greatly to the efficiency of the reaction. The mild reaction condition and wide substrate scope of the reaction will not only provide a useful strategy for solving the problems of residual metal and harsh reaction condition associated with metal catalysis, but also expand the applicability of organocatalytic reactions for the synthesis of 1,1-diarylethanes.
- Brønsted acid catalysis,
- organocatalysis,
- 1,1-diarylethane,
- ortho-hydroxylstyrene,
- indole,
- ortho-quinone methide
1. [1]
2. [2]
  Nakao, Y.; Kanyiva, K. S.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2006, 128, 8146. (b) Kanyiva, K. S.; Nakao, Y.; Hiyama, T. Heterocycles 2007, 72, 677. (c) Wang, M.-Z.; Wong, M.-K.; Che, C.-M. Chem. Eur. J. 2008, 14, 8353. (d) Xiao, Y.-P.; Liu, X.-Y.; Che, C.-M. J. Organomet.Chem. 2009, 694, 494. (e) Nakao, Y.; Kashihara, N.; Kanyiva, K. S.; Hiyama, T. Angew. Chem., Int. Ed. 2010, 49, 4451. (f) Zhou, F.; Cao, Z.-Y.; Zhang, J.; Yang, H.-B.; Zhou, J. Chem. Asian J.2012, 7, 233. (g) Chen, L.; Zhou, J. Chem. Asian J. 2012, 7, 2510.
3. [3]
  Pathak, T. P.; Sigman, M. S. Org. Lett. 2011, 13, 2774.
4. [4]
  Zheng, C.; You, S.-L. Chem. Soc.Rev.2012, 41, 2498; (b) Pellissier, H. Adv. Synth. Catal.2012, 354, 237.
5. [5]
  Akiyama, T. Chem.Rev.2007, 107, 5744. (b) Terada, M. Chem. Commun.2008, 4097. (c) Terada, M. Synthesis2010, 1929. (d) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res.2011, 44, 1156. (e) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M. Chem.Rev.2014, 114, 9047. (f) Huang, J.; Luo, S.; Gong, L. Acta Chim. Sinica2013, 71, 879.
6. [6]
  Tan, W.; Li, X.; Gong, Y.-X.; Ge, M.-D.; Shi, F. Chem.Commun. 2014, 50, 15901. (b) Zhang, Y.-C.; Zhao, J.-J.; Jiang, F.; Sun, S.-B.; Shi, F. Angew. Chem., Int. Ed. 2014, 53, 13912. (c) Zhao, J.-J.; Sun, S.-B.; He, S.-H.; Wu, Q.; Shi, F. Angew. Chem., Int. Ed.2015, 54, 5460.
7. [7]
  Dai, W.; Lu, H.; Jiang, X.-L.; Gao, T.-T.; Shi, F. Tetrahedron: Asymmetry 2015, 26, 109.
8. [8]
  Wang, Z.-B.; Ai, F.-J.; Wang, Z.; Zhao,W.-X.; Zhu, G.-Y.; Lin, Z.-Y.; Sun, J.-W. J. Am.Chem. Soc. 2015, 137, 383.
9. [9]
  Li, M.-L.; Chen, D.-F.; Luo, S.-W.; Wu, X. Tetrahedron: Asymmetry 2015, 26, 219.
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沈阳化工大学材料科学与工程学院沈阳 110142