Citation: Qiao Huijie, Sun Suyan, Kang Jianxun, Yang Fan, Wu Yusheng, Wu Yangjie. Copper-Catalyzed Decarboxylative Coupling of Alkenyl Acids with P(O)H Compounds at Room Temperature[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 86-94. doi: 10.6023/cjoc201708049 shu

Copper-Catalyzed Decarboxylative Coupling of Alkenyl Acids with P(O)H Compounds at Room Temperature

Qiao Huijie ^a ,
Sun Suyan ^a ,
Kang Jianxun ^a ,
Yang Fan ^a,, ,
Wu Yusheng ^b,c,, ,
Wu Yangjie ^a,,

a.
College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052
b.
Tetranov Biopharm, LLC., Zhengzhou 450052
c.
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001

Corresponding author: Yang Fan, yangf@zzu.edu.cn Wu Yusheng, yusheng.wu@tetranovglobal.com Wu Yangjie, wyj@zzu.edu.cn
Received Date: 23 August 2017
Revised Date: 20 September 2017
Available Online: 26 January 2017
Fund Project: the National Natural Science Foundation of China 21172200the National Natural Science Foundation of China 21102134Project supported by the National Natural Science Foundation of China (Nos. 21102134, 21172200)

Figures(3)

A simple and mild protocol for the copper-catalyzed decarboxylative coupling of alkenyl acids with P(O)H compounds was developed, thus providing a facile route to the vinylphosphorus compounds. Moreover, the reaction could also afford β-ketophosphorus compounds as the major products in air using oxygen as an oxidant. In addition, the remarkable features of these two types of reactions include excellent reaction chemoselectivity, good functional group tolerance and mild reaction conditions (e.g., cheap oxidant, ligand-free condition and room temperature).
- copper catalysis,
- decarboxylative coupling,
- alkenyl acids,
- P(O)H compounds
1. [1]
  (a) Minami, T. ; Motoyoshiya, J. Synthesis 1992, 333.
  (b) Wang, H. -Q. ; Liu, Z. -J. Chin. J. Org. Chem. 2003, 23, 321.
2. [2]
  (a) Jin, S. ; Gonsalves, K. E. Macromolecules 1998, 31, 1010.
  (b) Price, D. ; Pyrah, K. ; Hull, T. R. ; Milnes, G. J. ; Ebdon, J. R. ; Hunt, B. J. ; Joseph, P. Polym. Degrad. Stab. 2002, 77, 227.
3. [3]
  (a) Harnden, M. R. ; Parkin, A. ; Parratt, M. J. ; Perkins, R. M. J. Med. Chem. 1993, 36, 1343.
  (b) Lazrek, H. B. ; Rochdi, A. ; Khaider, H. ; Barascut, J. -L. ; Imbach, J. -L. ; Balzarini, J. ; Witvrouw, M. ; Pannecouque, C. ; De Clercq, E. Tetrahedron 1998, 54, 3807.
4. [4]
  (a) Chatterjee, A. K. ; Choi, T. -L. ; Grubbs, R. H. Synlett 2001, 1034.
  (b) Bisaro, F. ; Gouverneur, V. Tetrahedron Lett. 2003, 44, 7133.
  (c) Vinokurov, N. ; Michrowska, A. ; Szmigielska, A. ; Drzazga, Z. ; Wójciuk, G. ; Demchuk, O. M. ; Grela, K. ; Pietrusiewicz, K. M. ; Butensch n, H. Adv. Synth. Catal. 2006, 348, 931.
5. [5]
  (a) Al-Maksoud, W. ; Mesnager, J. ; Jaber, F. ; Pinel, C. ; Djakovitch, L. J. Organomet. Chem. 2009, 694, 3222.
  (b) Burini, A. ; Cacchi, S. ; Pace, P. ; Pietroni, B. R. Synlett 1995, 677.
  (c) Kabalka, G. W. ; Guchhait, S. K. ; Naravane, A. Tetrahedron Lett. 2004, 45, 4685.
6. [6]
  (a) Mao, L. -L. ; Zhou, A. -X. ; Liu, N. ; Yang, S. -D. Synlett 2014, 25, 2727.
  (b) Gui, Q. ; Hu, L. ; Chen, X. ; Liu, J. ; Tan, Z. Chem. Commun. 2015, 51, 13922.
  (c) Zhang, G. -Y. ; Li, C. -K. ; Li, D. -P. ; Shoberu, A. ; Zou, J. -P. Tetrahedron 2016, 72, 2972.
  (d) Peng, P. ; Lu, Q. ; Peng, L. ; Liu, C. ; Wang. G. ; Lei, A. Chem. Commun. 2016, 52, 12338.
  (e) Gu, J. ; Cai, C. Org. Biomol. Chem. 2017, 15, 4226.
7. [7]
  (a) Russell, G. A. ; Ngoviwatchai, P. ; Tashtoush, H. I. ; Pla-Dalmau, A. ; Khanna, R. K. J. Am. Chem. Soc. 1988, 110, 3530. (b(c) Evano, G. ; Tadiparthi, K. ; Couty, F. Chem. Commun. 2011, 47, 179.
  (d) Xu, K. ; Hu, H. ; Yang, F. ; Wu, Y. Eur. J. Org. Chem. 2013, 319.
  (e) Jouvin, K. ; Coste, A. ; Bayle, A. ; Legrand, F. ; Karthikeyan, G. ; Tadiparthi, K. ; Evano, G. Organometallics 2012, 31, 7933.
  (f) Liu, L. ; Wang, Y. ; Zeng, Z. ; Xu, P. ; Gao, Y. ; Yin, Y. ; Zhao, Y. Adv. Synth. Catal. 2013, 355, 659.
  (g) Iranpoor, N. ; Firouzabadi, H. ; Moghadam, K. R. ; Motavalli, S. RSC Adv. 2014, 4, 55732.
8. [8]
  Lin, Y.; Lu, G.; Wang, R.; Yi, W. Org. Lett. 2017, 19, 1100. doi: 10.1021/acs.orglett.7b00126
9. [9]
  (a) Kabalka, G. W. ; Guchhait, S. K. Org. Lett. 2003, 5, 729.
  (b) Zhuang, R. ; Xu, J. ; Cai, Z. ; Tang, G. ; Fang, M. ; Zhao, Y. Org. Lett. 2011, 13, 2110.
10. [10]
  (a) Xue, J. -F. ; Zhou, S. -F. ; Liu, Y. -Y. ; Pan, X. ; Zou, J. -P. ; Asekun, O. T. Org. Biomol. Chem. 2015, 13, 4896.
  (b) Yuan, J. -W. ; Yang, L. -R. ; Mao, P. ; Qu, L. -B. RSC Adv. 2016, 6, 87058.
  (c) Yuan, J. -W. ; Li, Y. -Z. ; Mai, W. -P. ; Yang, L. -R. ; Qu, L. -B. Tetrahedron 2016, 72, 3084.
11. [11]
  Thielges, S.; Bisseret, P.; Eustache, J. Org. Lett. 2005, 7, 681. doi: 10.1021/ol047516y
12. [12]
  (a) Han, L. -B. ; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
  (b) Zhao, C. -Q. ; Han, L. -B. ; Goto, M. ; Tanaka, M. Angew. Chem. Int. Ed. 2001, 40, 1929.
  (c) Han, L. -B. ; Zhao, C. -Q. ; Onozawa, S. -Y. ; Goto, M. ; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842.
  (d) Lai, C. ; Xi, C. ; Chen, C. ; Ma, M. ; Hong, X. Chem. Commun. 2003, 2736.
  (e) Han, L. -B. ; Zhang, C. ; Yazawa, H. ; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080.
  (f) Kuramshin, A. I. ; Nikolaev, A. A. ; Cherkasov, R. A. Mendeleev Commun. 2005, 15, 155.
  (g) Nune, S. K. ; Tanaka, M. Chem. Commun. 2007, 2858.
  (h) Niu, M. ; Fu, H. ; Jiang, Y. ; Zhao, Y. Chem. Commun. 2007, 272.
  (i) Han, L. -B. ; Ono, Y. ; Shimada, S. J. Am. Chem. Soc. 2008, 130, 27.
  (j) Ananikov, V. P. ; Khemchyan, L. L. ; Beletskaya, I. P. ; Starikova, Z. A. Adv. Synth. Catal. 2010, 352, 2979.
  (k) Khemchyan, L. L. ; Lvanova, J. V. ; Zalesskiy, S. S. ; Ananikov, V. P. ; Beletskaya, I. P. ; Starikova, Z. A. Adv. Synth. Catal. 2014, 356, 771.
  (l) Liu, L. ; Wu, Y. ; Wang, Z. ; Zhu, J. ; Zhao, Y. J. Org. Chem. 2014, 79, 6816.
  (m) Braun, R. A. ; Bradfield, J. L. ; Henderson, C. B. ; Mobarrez, N. ; Sheng, Y. ; O'Brien, R. A. ; Stenson, A. C. ; Davis Jr., J. H. ; Mirjafari, A. Green Chem. 2015, 17, 1259.
13. [13]
  (a) Borah, A. J. ; Yan, G. Org. Biomol. Chem. 2015, 13, 8094.
  (b) Chary, V. S. ; Rajanna, K. C. ; Krishnaiaha, G. ; Srinivas, P. Catal. Sci. Technol. 2016, 6, 1430.
  (c) Cai, S. ; Xu, Y. ; Chen, D. ; Li, L. ; Chen, Q. ; Huang, M. ; Weng, W. Org. Lett. 2016, 18, 2990.
  (d) Zhang, H. -R. ; Chen, D. -Q. ; Han, Y. -P. ; Qiu, Y. -F. ; Jin, D. -P. ; Liu, X. -Y. Chem. Commun. 2016, 52, 11827.
  (e) Kadari, L. ; Palakodety, R. K. ; Yallapragada, L. P. Org. Lett. 2017, 19, 2580.
14. [14]
  Hu, J.; Zhao, N.; Yang, B.; Wang, G.; Guo, L.-N.; Liang, Y.-M.; Yang, S.-D. Chem.-Eur. J. 2011, 17, 5516. doi: 10.1002/chem.v17.20
15. [15]
  Wu, Y.; Liu, L.; Yan, K.; Xu, P.; Gao, Y.; Zhao Y. J. Org. Chem. 2014, 79, 8118. doi: 10.1021/jo501321m
16. [16]
  Qiao, H.; Sun, S.; Zhang, Y.; Zhu, H.; Yu, X.; Yang, F.; Wu, Y.; Li, Z.; Wu, Y. Org. Chem. Front. 2017, 4, 1981. doi: 10.1039/C7QO00305F
17. [17]
  Li, Y.; Das, S.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2012, 134, 9727. doi: 10.1021/ja301764m
18. [18]
  Hu, G.; Gao, Y.; Zhao, Y. Org. Lett. 2014, 16, 4464. doi: 10.1021/ol502009b
19. [19]
  Kondoh, A; Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2008, 81, 502. doi: 10.1246/bcsj.81.502
20. [20]
  Harmata, M.; Rayanil, K.; Espejo, V. R.; Barnes, C. L. J. Org. Chem. 2009, 74, 3214. doi: 10.1021/jo900151d
21. [21]
  Ke, J.; Tang, Y.; Yi, H.; Li, Y.; Cheng, Y.; Liu, C.; Lei, A. Angew. Chem. Int. Ed. 2015, 54, 6604. doi: 10.1002/anie.201501287
22. [22]
  Zhang, P.; Zhang, L.; Gao, Y.; Xu, J.; Fang, H.; Tang, G.; Zhao, Y. Chem. Commun. 2015, 51, 7839. doi: 10.1039/C5CC01904D
23. [23]
  Miyaji, T.; Xi, Z.; Ogasawara, M.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2007, 72, 8737. doi: 10.1021/jo071089v
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