研究论文

镍催化的偕二氟芳基乙烯与有机锌交叉偶联反应立体选择性合成(Z)-单氟烯烃

  • 张娟 ,
  • 王碧云 ,
  • 刘熠森 ,
  • 曹松
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  • 上海市化学生物学(芳香杂环)重点实验室 华东理工大学药学院 上海 200237

收稿日期: 2018-07-06

  修回日期: 2018-09-05

  网络出版日期: 2018-09-18

基金资助

国家自然科学基金(Nos.21472043,21272070)资助项目.

Stereoselective Synthesis of Z-Fluorostyrene Derivatives via Nickel-Catalyzed Cross-Coupling of gem-Difluorostyrenes with Organozinc Reagents

  • Zhang Juan ,
  • Wang Biyun ,
  • Liu Yisen ,
  • Cao Song
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  • Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology(ECUST), Shanghai 200237

Received date: 2018-07-06

  Revised date: 2018-09-05

  Online published: 2018-09-18

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21472043, 21272070).

摘要

报道了在NiCl2(dppp)催化和氯化锂促进下,室温下将偕二氟芳基乙烯与有机锌试剂进行交叉偶联反应,合成一系列(Z)-单氟烯烃的方法.该方法具有反应条件温和、操作简单、官能团兼容性较好、立体选择性出色等优点.

本文引用格式

张娟 , 王碧云 , 刘熠森 , 曹松 . 镍催化的偕二氟芳基乙烯与有机锌交叉偶联反应立体选择性合成(Z)-单氟烯烃[J]. 有机化学, 2019 , 39(1) : 249 -256 . DOI: 10.6023/cjoc201807013

Abstract

An efficient method for the synthesis of various Z-fluorostyrene derivatives via nickel-catalyzed cross-coupling of gem-difluorostyrenes with organozinc reagents with the assistance of LiCl was developed. The reaction proceeds efficiently under mild condition, affording monofluoroalkenes in moderate to good yields. This novel method exhibits good functional group compatibility and excellent stereoselectivity.

参考文献

[1] (a) Landelle, G.; Bergeron, M.; Turcotte-Savard, M.-O.; Paquin, J.-F. Chem. Soc. Rev. 2011, 40, 2867.
(b) Malo-Forest, B.; Landelle, G.; Roy, J.-A.; Lacroix, J.; Gaudreault, R. C.; Paquin, J.-F. Bioorg. Med. Chem. Lett. 2013, 23, 1712.
(c) Zhao, Y.-C.; Jiang, F.-Z. Hu, J.-B. J. Am. Chem. Soc. 2015, 137, 5199.
(d) Eddarir, S.; Abdelhadi, Z.; Rolando, C. Tetrahedron Lett. 2001, 42, 9127.
(e) Liao, F.-M.; Yu, J.-S.; Zhou, J. Chin. J. Org. Chem. 2017, 37, 2175(in Chinese). (廖富民, 余金生, 周剑, 有机化学, 2017, 37, 2175.)
(f) Chen, X.-W.; Gan, X.-H.; Chen, J.-X.; Chen, Y.-Z.; Wang, Y.-J.; Hu, D.-Y.; Song, B.-A. Chin. J. Org. Chem. 2017, 37, 2343(in Chinese). (陈学文, 甘秀海, 陈吉祥, 陈永中, 王艳娇, 胡德禹, 宋宝安, 有机化学, 2017, 37, 2343.)
[2] (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.
[3] (a) Udagawa, T.; Kogawa, M.; Tsuchi, Y.; Watanabe, H.; Yamamoto, M.; Kawatsura, M. Tetrahedron Lett. 2017, 58, 227.
(b) Augustine, J. K.; Boodappa, C.; Venkatachaliah, S. Org. Biomol. Chem. 2014, 12, 2280.
(c) Kogawa M.; Watanabe, H.; Yamamoto, M.; Tsuchi, Y.; Zhou, B.; Kawatsura, M. Synlett 2017, 28, 1071.
(d) Liu, Y.-L.; Zhou, J. Acta Chim. Sinica 2012, 70, 1451(in Chinese). (刘运林, 周剑, 化学学报, 2012, 70, 1451.)
(e) Liu, Y.; Deng, M.-M.; Zhang, Z.-Y.; Ding, X.-H.; Dai, Z.-Q.; Guan, J.-T. Chin. J. Org. Chem. 2012, 32, 661(in Chinese). (刘运, 邓萌萌, 张智勇, 丁肖华, 戴志群, 关金涛, 有机化学, 2012, 32, 661.)
[4] (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.
[5] (a) Hara, S. Top. Curr. Chem. 2012, 327, 59.
(b) Zhang, X.-X.; Cao, S. Tetrahedron Lett. 2017, 58, 375.
[6] (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.
[7] 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.
[8] Kojima, R.; Kubota, K.; Ito, H. Chem. Commun. 2017, 53, 10688.
[9] Kong, L-H.; Liu, B.-X.; Zhou, X.-K.; Wang, F.; Li, X.-W. Chem. Commun. 2017, 53, 10326.
[10] 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.
[11] (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.
[12] Gerber, R.; Frech, C. M. Chem. Eur. J. 2011, 17, 11893.
[13] Yang, Y.; Oldenhuis, N. J.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 615.
[14] (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.
[15] Saeki, T.; Takashima, Y.; Tamao, K. Synlett 2005, 1771.
[16] Ohashi, M.;Kambara, T.; Hatanaka, T.; Saijo, H.; Doi, R.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 3256.
[17] Ohashi, M.; Kamura, R.; Doi, R.; Ogoshi, S. Chem. Lett. 2013, 42, 933.
[18] (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.
[19] (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.
[20] (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.
[21] Qiu, J.; Gyorokos, A.; Tarasow, T. M.; Guiles, J. J. Org. Chem. 2008, 73, 9775.
[22] Ohashi, M.; Saijo, H.; Shibata, M.; Ogoshi, S. Eur. J. Org. Chem. 2013, 443.
[23] (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.
[24] Shi, H.-Y.; Dai, W.-P.; Wang, B.-Y.; Cao, S. Organometallics 2018, 37, 459.
[25] Thomoson, C. S.; Martinez, H.; Dolbier Jr, W. R. J. Fluorine Chem. 2013, 150, 53.
[26] Ji, Y.; Zhong, N.; Kang, Z.-N.; Yan, G.-B.; Zhao, M. Synlett 2018, 29, 209.
[27] Shao, Q.; Huang, Y. Chem. Commun. 2015, 51, 6584.
[28] Wenz, J.; Rettenmeier, C. A.; Wadepohl, H.; Gade, L. H. Chem. Commun. 2016, 52, 202.
[29] Eric, R.; Mouâd, A.; Gérard, C. J. Organomet. Chem. 2001, 624, 376.
[30] Loefflerx, L. J.; Delorefice, S. B. J. Pharm. Sci. 1975, 64, 1170.
[31] Kim, S. P.; Yang, J. Y.; Kang, M. Y.; Park, J. C.; Nam, S. H.; Friedman, M. J. Agric. Food Chem. 2011, 59, 4570.

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