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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 1: 86 - 94

DOI: https://doi.org/10.6023/cjoc201708049

Articles

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

  • Qiao Huijie ,
  • Sun Suyan ,
  • Kang Jianxun ,
  • Yang Fan ,
  • Wu Yusheng ,
  • Wu Yangjie
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  • 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

Received date: 2017-08-23

  Revised date: 2017-09-20

  Online published: 2017-09-26

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21102134, 21172200).

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Abstract

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).

Key words： copper catalysis; decarboxylative coupling; alkenyl acids; P(O)H compounds

Cite this article

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

References

[1] (a) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
(b) Wang, H.-Q.; Liu, Z.-J. Chin. J. Org. Chem. 2003, 23, 321.
[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] (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] (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.; Butenschön, H. Adv. Synth. Catal. 2006, 348, 931.
[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] (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] (a) Russell, G. A.; Ngoviwatchai, P.; Tashtoush, H. I.; Pla-Dalmau, A.; Khanna, R. K. J. Am. Chem. Soc. 1988, 110, 3530.
(b) Kobayashi, Y.; William, A. D. Adv. Synth. Catal. 2004, 346, 1749.
(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] Lin, Y.; Lu, G.; Wang, R.; Yi, W. Org. Lett. 2017, 19, 1100.
[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] (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] Thielges, S.; Bisseret, P.; Eustache, J. Org. Lett. 2005, 7, 681.
[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] (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] Hu, J.; Zhao, N.; Yang, B.; Wang, G.; Guo, L.-N.; Liang, Y.-M.; Yang, S.-D. Chem.-Eur. J. 2011, 17, 5516.
[15] Wu, Y.; Liu, L.; Yan, K.; Xu, P.; Gao, Y.; Zhao Y. J. Org. Chem. 2014, 79, 8118.
[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.
[17] Li, Y.; Das, S.; Zhou, S.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2012, 134, 9727.
[18] Hu, G.; Gao, Y.; Zhao, Y. Org. Lett. 2014, 16, 4464.
[19] Kondoh, A; Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2008, 81, 502.
[20] Harmata, M.; Rayanil, K.; Espejo, V. R.; Barnes, C. L. J. Org. Chem. 2009, 74, 3214.
[21] Ke, J.; Tang, Y.; Yi, H.; Li, Y.; Cheng, Y.; Liu, C.; Lei, A. Angew. Chem. Int. Ed. 2015, 54, 6604.
[22] Zhang, P.; Zhang, L.; Gao, Y.; Xu, J.; Fang, H.; Tang, G.; Zhao, Y. Chem. Commun. 2015, 51, 7839.
[23] Miyaji, T.; Xi, Z.; Ogasawara, M.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2007, 72, 8737.

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