SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 2: 532 - 537

DOI: https://doi.org/10.6023/cjoc201807024

Notes

Anhydride Induced One-Pot Synthesis of ortho-Acyloxy Diarylalkenes from 2-(1-Hydroxy-1-arylalkyl)phenols

Expand
  • a School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237;
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2018-07-16

  Revised date: 2018-09-04

  Online published: 2018-09-26

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372075) and the Shanghai Pujiang Program (No. 16PJD017).

Fold

Abstract

Reaction of 2-(1-hydroxy-1-arylalkyl)phenols with anhydride and NEt3 was reported, providing a practical way to the synthesis of ortho-acyloxy diarylalkenes, which is an important motif in many bioactive compounds and starting materials in many organic synthesis. This reaction can be achieved in one pot reaction under mild conditions in good yields.

Key words： 2-(1-hydroxy-1-arylalkyl)phenols; ortho-acyloxy diarylalkenes; mild conditions; anhydride promoted reaction

Cite this article

Lü Wenwena, He Xinchuna, Shi Mina, Wang Feijun . Anhydride Induced One-Pot Synthesis of ortho-Acyloxy Diarylalkenes from 2-(1-Hydroxy-1-arylalkyl)phenols[J]. Chinese Journal of Organic Chemistry, 2019 , 39(2) : 532 -537 . DOI: 10.6023/cjoc201807024

References

[1] Jain, N. K.; Krishnamurty, H. G. Indian J. Chem., Sect. B 2000, 39, 817.
[2] Arnone, A.; Modugno, V. D.; Nasini, G.; Pava, O. V. Gazz. Chim. Ital. 1990, 120, 397.
[3] Shaiq, A. M.; Shaukat, M.; Shaista, P.; Uddin, A. U.; Hafeez, G. Phytochemistry 1999, 50, 1385.
[4] (a) Zheng, Y.-L.; Liu, Y.-Y.; Wu, Y.-M.; Wang, Y.-X. Lin, Y.-T.; Ye, M.-C. Angew. Chem., Int. Ed. 2016, 55, 6315.
(b) Botteghi, C.; Corrias, T.; Marchetti, M.; Paganelli, S.; Piccolo, O. Org. Process Res. dev. 2002, 6, 379.
[5] (a) Zhang, Z.; Ju, T.; Miao, M.; Han, J.-L.; Zhang, Y.-H.; Zhu, X.-Y.; Ye, J.-H.; Yu, D.-J.; Zhi, Y.-G. Org. Lett. 2017, 19, 396.
(b) Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.
(c) Li, J.-F.; Chang, W.-J.; Ren, W.-L.; Liu, W.; Wang, H.-N.; Shi, Y. Org. Biomol. Chem. 2015, 13, 10341.
[6] (a) Ghorai, J.; Reddy, A. C. S.; Anbarasan, P. Chem.-Eur. J. 2016, 22, 16042.
(b) Yang, D.-J.; Zhu, Y.-F.; Yang, N.; Jiang, Q.-Q.; Liu, R.-H. Adv. Synth. Catal. 2016, 358, 1731.
(c) Chang, M.-Y.; Huang, Y.-H.; Wang, H.-S. Tetrahedron 2016, 72, 3022.
[7] (a) Han, Y.-P.; Song, X.-R.; Qiu, Y.-F.; Li, X.-S.; Zhang, H.-R.; Zhu, X.-Y.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 3866.
(b) Casanova, N.; Seoane, A.; MascareÇas, J. L.; Gulias, M. Angew. Chem., Int. Ed. 2015, 54, 2374.
[8] (a) Wang, Z.-B.; Ai, F.-J.; Wang, Z.; Zhao, W.-X.; Zhu, G.-G.; Lin, Z.-Y.; Sun, J.-W. J. Am. Chem. Soc. 2015, 137, 383.
(b) Chen, J.-H.; Chen, C.-H.; Ji, C.-L.; Lu, Z. Org. Lett. 2016, 18, 1594.
[9] Nicolaou, K. C.; Snyder, S. A.; Huang, X.-H.; Simonsen, K. B.; Koumbis, A. E.; Bigot, A. J. Am. Chem. Soc. 2004, 126, 10162.
[10] Kaswan, P.; Shelke, M. G.; Rao, K. V.; Kumar, A. Synlett 2016, 27, 2553.
[11] Wang, Z.-N.; He, X.-X.; Zhang, R.; Zhang, G.; Xu, G. X.; Zhang, Q.; Xiong, T.; Zhang, Q. Org. Lett. 2017, 19, 3067.
[12] Han, P.; Wang, R.-J.; Wang, D. Z. Tetrahedron 2011, 67, 8873.
[13] Zhang, Q.; Zheng, G.-F.; Zhang, Q; Li, Y. J. Org. Chem. 2017, 82, 8258.
[14] Xie, J.; Li, J.; Weingand, V.; Rudolph, M.; Hashmi, A. S. K. Chem.-Eur. J. 2016, 22, 12646.
[15] Moure, M. J.; Martin, R. S.; Dominguez, E. Angew. Chem., Int. Ed. 2012, 57, 3220.
[16] (a) Haldar, S.; Koner, S. Beilstein J. Org. Chem. 2013, 9, 49.
(b) Tochigi, A.; Tsukamoto, K.; Suzuki, N.; Masuyama, Y. Eur. J. Org. Chem. 2016, 5678.
[17] Chang, M.-Y.; Huang, Y.-H.; Wang, H.-S. Tetrahedron 2016, 72, 3022.
[18] Zou, Y.-J.; Qin, L.-N.; Ren, X.-F.; Lu, Y.-P.; Li, Y.-X.; Zhou, J.-R. Chem. Eur. J. 2013, 19, 3504.
[19] Berthiol, F.; Doucet, H.; Santelli, M. Eur. J. Org. Chem. 2003, 1091.
[20] Hamze, A.; Veau, D.; Provot, O.; Brion, J. D.; Alami, M. J. Org. Chem. 2009, 74, 1337.
[21] Roche, M.; Hamze, A.; Provot, O.; Brion, J. D.; Alami, M. J. Org. Chem. 2013, 78, 445.
[22] (a) Zhang, Y.; He, Y.; Li, L.-S.; Ji, M.-M.; Li, X.-Z.; Zhu, G.-G. J. Org. Chem. 2018, 83, 2898.
(b) Hu, F.-D.; Xia, Y.; Ye, F.; Liu, Z.-X.; Ma, C.; Zhang, Y.; Wang, J.-B. Angew. Chem., Int. Ed. 2014, 53, 1364.
[23] Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.
[24] (a) Brady, W. T.; Giang, Y. F. J. Org. Chem. 1985, 50, 5177.
(b) Wang, Z.-B.; Ai, F.-J.; Wang, Z.; Zhao, W.-X.; Zhu, G.-Y.; Lin, Z.-Y.; Sun, Z.-W. J. Am. Chem. Soc. 2015, 137, 383.
(c) Ogawa, N.; Yamaoka, Y.; Yamada, K.; Takasu, K. Org. Lett. 2017, 19, 3327.
[25] (a) Chiang, Y.; Jerry, K. A. Org. Biomol. Chem. 2004, 2, 1090.
(b) Uchida, M.; Kuma, M.; Irie, M. Bull. Chem. Soc. Jpn. 1996, 69, 1023.
(c) Guo, L.; Zhang, F.-Y.; Hu, W.-M.; Lia, L.; Jia, Y.-X. Chem. Commun. 2014, 50, 3299.
(d) Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.
[26] Hull, F. J.; Balcells, D.; Sauer, L. O. E.; Raynaud, C.; Brudvig, W. G.; Crabtree, H. R.; Eisenstein, O. J. Am. Chem. Soc. 2010, 132, 7605.
[27] Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.

Options
Outlines

/

〈 〉