Stereoselective Synthesis of Z-Fluorostyrene Derivatives via Nickel-Catalyzed Cross-Coupling of gem-Difluorostyrenes with Organozinc Reagents
- Corresponding author: Cao Song, scao@ecust.edu.cn
Citation:
Zhang Juan, Wang Biyun, Liu Yisen, Cao Song. Stereoselective Synthesis of Z-Fluorostyrene Derivatives via Nickel-Catalyzed Cross-Coupling of gem-Difluorostyrenes with Organozinc Reagents[J]. Chinese Journal of Organic Chemistry,
;2019, 39(1): 249-256.
doi:
10.6023/cjoc201807013
(a) Laue, K. W.; Mück-Lichtenfeld, C.; Haufe, G. Tetrahedron 1999, 55, 10413.
(b) Guérin, D.; Dez, I.; Gaumont, A. C.; Pannecoucke, X.; Couve-Bonnaire, S. Org. Lett. 2016, 18, 3606.
(a) Drouin, M.; Hamel, J.-D.; Paquin J.-F. Synthesis 2018, 50, 881.
(b) Koh, M. J.; Nguyen, T. T.; Zhang, H.; Schrock, R. R.; Hoveyda, A. H. Nature 2016, 531, 459.
(a) Hara, S. Top. Curr. Chem. 2012, 327, 59.
(b) Zhang, X.-X.; Cao, S. Tetrahedron Lett. 2017, 58, 375.
(a) Hu, J.-F.; Han, X.-W.; Yuan, Y.; Shi, Z.-Z. Angew. Chem., Int. Ed. 2017, 56, 13342.
(b) Kong, L.-H.; Zhou, X.-K.; Li, X.-W. Org. Lett. 2016, 18, 6320.
Cai, S.-H.; Ye, L.; Wang, D.-X.; Wang, Y.-Q.; Lai, L.-J.; Zhu, C.; Feng, C.; Loh, T.-P. Chem. Commun. 2017, 53, 8731.
doi: 10.1039/C7CC04131D
Kojima, R.; Kubota, K.; Ito, H. Chem. Commun. 2017, 53, 10688.
doi: 10.1039/C7CC05225A
Kong, L-H.; Liu, B.-X.; Zhou, X.-K.; Wang, F.; Li, X.-W. Chem. Commun. 2017, 53, 10326.
doi: 10.1039/C7CC06048C
Lu, X.; Wang, Y.; Zhang, B.; Pi, J.-J.; Wang, X.-X.; Gong, T.-J.; Xiao, B.; Fu, Y. J. Am. Chem. Soc. 2017, 139, 12632.
doi: 10.1021/jacs.7b06469
(a) Negishi, E.-I. Angew. Chem., Int. Ed. 2011, 50, 6738.
[b] Wang, K.; Kong, W. Q. Chin. J. Chem. 2018, 36, 247.
[c] Zhang, P.-C.; Wang Y. D.; Qian, D. Y.; Li, W. B.; Zhang, J. L. Chin. J. Chem. 2017, 35, 849.
Gerber, R.; Frech, C. M. Chem. Eur. J. 2011, 17, 11893.
doi: 10.1002/chem.v17.42
Yang, Y.; Oldenhuis, N. J.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 615.
doi: 10.1002/anie.201207750
(a) Sun, A. D.; Leung, K.; Restivo, A. D.; LaBerge, N. A.; Takasaki, H.; Love, J. A. Chem.-Eur. J. 2014, 20, 3162.
(b) Zhu, F.; Wang, Z.-X. J. Org. Chem. 2014, 79, 4285.
(c) Xiao, S.-H.; Xiong, Y.; Zhang, X.-X.; Cao, S. Tetrahedron 2014, 70, 4405.
Ohashi, M.; Kambara, T.; Hatanaka, T.; Saijo, H.; Doi, R.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 3256.
doi: 10.1021/ja109911p
Ohashi, M.; Kamura, R.; Doi, R.; Ogoshi, S. Chem. Lett. 2013, 42, 933.
doi: 10.1246/cl.130294
(a) Xiong, Y.; Huang, T.; Ji, X.-F.; Wu, J.-J., Cao, S. Org. Biomol. Chem. 2015, 13, 7389.
(b) Zhang, J.; Xu, C.-Y.; Wu, W.; Cao, S. Chem. Eur. J. 2016, 22, 9902.
(c) Zhang, J.; Dai, W.-P.; Liu, Q.-Y.; Cao, S. Org. Lett. 2017, 19, 3283.
(a) Dai, W.-P.; Xiao, J.; Jin, G.-Y.; Wu, J.-J.; Cao, S. J. Org. Chem. 2014, 79, 10537.
(b) Dai, W.-P.; Shi, H.-Y.; Zhao, X.-H.; Cao, S. Org. Lett. 2016, 18, 4284.
(a) Zeng, X.-Z.; Qian, M.-X.; Hu, Q.; Negishi, E.-I. Angew. Chem., Int. Ed. 2004, 43, 2259.
(b) Tan, Z.; Negishi, E.-I. Angew. Chem., Int. Ed. 2006, 45, 762.
Qiu, J.; Gyorokos, A.; Tarasow, T. M.; Guiles, J. J. Org. Chem. 2008, 73, 9775.
doi: 10.1021/jo801647x
Ohashi, M.; Saijo, H.; Shibata, M.; Ogoshi, S. Eur. J. Org. Chem. 2013, 443.
(a) Thornbury, R. T.; Toste, F. D. Angew. Chem., Int. Ed. 2016, 55, 11629.
(b) Ichikawa, J.; Sakoda, K.; Mihara, J.; Ito, N. J. Fluorine Chem. 2006, 127, 489.
Shi, H.-Y.; Dai, W.-P.; Wang, B.-Y.; Cao, S. Organometallics 2018, 37, 459.
doi: 10.1021/acs.organomet.7b00859
Thomoson, C. S.; Martinez, H.; Dolbier Jr, W. R. J. Fluorine Chem. 2013, 150, 53.
doi: 10.1016/j.jfluchem.2013.02.026
Ji, Y.; Zhong, N.; Kang, Z.-N.; Yan, G.-B.; Zhao, M. Synlett 2018, 29, 209.
doi: 10.1055/s-0036-1590907
Shao, Q.; Huang, Y. Chem. Commun. 2015, 51, 6584.
doi: 10.1039/C5CC01407G
Wenz, J.; Rettenmeier, C. A.; Wadepohl, H.; Gade, L. H. Chem. Commun. 2016, 52, 202.
doi: 10.1039/C5CC08950F
Eric, R.; Mou ȃd, A.; Gérard, C. J. Organomet. Chem. 2001, 624, 376.
doi: 10.1016/S0022-328X(00)00891-3
Loefflerx, L. J.; Delorefice, S. B. J. Pharm. Sci. 1975, 64, 1170.
doi: 10.1002/jps.2600640708
Kim, S. P.; Yang, J. Y.; Kang, M. Y.; Park, J. C.; Nam, S. H.; Friedman, M. J. Agric. Food Chem. 2011, 59, 4570.
doi: 10.1021/jf2003392
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