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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 2: 695 - 701

DOI: https://doi.org/10.6023/cjoc202008012

Article

Study on the Copper-Catalyzed Selective Allylation of Aryl (or Alkyl) Halides

  • Boshi Han ,
  • Zheng Shi ,
  • Huihong He ,
  • Xinghua Zhang
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  • a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418
    b Institute of Drug Discovery Technology, Ningbo University, Ningbo, Zhejiang 315211

Received date: 2020-08-10

  Revised date: 2020-09-17

  Online published: 2020-10-15

Supported by

the National Natural Science Foundation of China(21871182)

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Abstract

A practical method for the Cu-catalyzed coupling of aryl (or alkyl) halides with allylic acetates was described. This procedure effectively avoids the use of preformed Grignard reagent and affords allyl products with high to excellent regio- selectivity under relatively mild condition.

Key words： Keywords copper-catalyzed; allylation; regioselectivity

Cite this article

Boshi Han , Zheng Shi , Huihong He , Xinghua Zhang . Study on the Copper-Catalyzed Selective Allylation of Aryl (or Alkyl) Halides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 695 -701 . DOI: 10.6023/cjoc202008012

References

[1]
(a) Zhang Z.-Q.; Zhang B.; Lu X.; Liu J.-H.; Lu X.-Y.; Xiao B.; Fu Y. Org. Lett. 2016, 18, 952.
[1]
(b) Nguyen T. N. T.; Thiel N.O.; Pape F.; Teichert J.F. Org. Lett. 2016, 18, 2455.
[1]
(c) Xu G.; Zhao H.; Fu B.; Cang A.; Zhang G.; Xiong T.; Zhang Q. Angew. Chem. Int. Ed. 2017, 56, 13130.
[2]
(a) Trost B.M.; Van Vranken, D.L.Chem. Rev. 1996, 96, 395.
[2]
(b) Falciola C.A.; Alexakis A. Eur. J. Org. Chem. 2008, 22, 3765.
[2]
(c) Cui P.; Liu H.; Zhang D.; Wang C. Chin. J. Org. Chem. 2012, 32, 1401. (in Chinese)
[2]
崔朋雷, 刘海燕, 张冬暖, 王春, 有机化学, 2012, 32, 1401.).
[2]
(d) Deng Y.; Yang W.; Yang X.; Yang D. Chin. J. Org. Chem. 2017, 37, 3039. (in Chinese)
[2]
邓颖颖, 杨文, 杨新, 杨定乔, 有机化学, 2017, 37, 3039.).
[2]
(e) Zhang H.; Gu Q.; You S. Chin. J. Org. Chem. 2019, 39, 15. (in Chinese)
[2]
张慧君, 顾庆, 游书力, 有机化学, 2019, 39, 15.).
[3]
(a) Han X.; Zhang Y.; Wu J. J. Am. Chem. Soc. 2010, 132, 4104.
[3]
(b) Lauer A.M.; Mahmud F.; Wu J. J. Am. Chem. Soc. 2011, 133, 9119.
[3]
(c) Hornillos V.; Pérez M.; Fa?anás-Mastral M.; Feringa B.L. J. Am. Chem. Soc. 2013, 135, 2140.
[3]
(d) Magrez M.; Guen Y.L.; Baslé O.; Crévisy C.; Mauduit M. Chem. Eur. J. 2013, 19, 1199.
[4]
Liu J.-H.; Yang C.-T.; Lu X.-Y.; Zhang Z. -Q. Xu, L.; Cui, M.; Lu, X.; Xiao, B.; Fu, Y.; Liu, L.Chem. Eur. J. 2014, 20, 15334.
[5]
(a) Li Z.; Sun H.-M.; Shen Q. Org. Biomol. Chem. 2016, 14, 3314.
[5]
(b) Zhang J.; Lu G.; Xu J.; Sun H.; Shen Q. Org. Lett. 2016, 18, 2860.
[6]
(a) Czaplik W.M.; Mayer M.; Jacobi von Wangelin, A.Angew. Chem. Int. Ed. 2009, 48, 607.
[6]
(b) Mayer M.; Czaplik W.M.; Jacobi von Wangelin, A.Adv. Synth. Catal. 2010, 352, 2147.
[7]
(a) Cui X.; Wang S.; Zhang Y.; Deng W.; Qian Q.; Gong H. Org. Biomol. Chem. 2013, 11, 3094.
[7]
(b) Chen H.; Jia X.; Yu Y.; Gong H. Angew. Chem. Int. Ed. 2017, 56, 13103.
[8]
Anka-Lufford L.L.; Prinsell M.R.; Weix D.J. J. Org. Chem. 2012, 77, 9989.
[9]
Qian X.; Auffrant A.; Felouat A.; Gosmini C. Angew. Chem. Int. Ed. 2011, 50, 10402.
[10]
Liu Y.; Fang Y.; Zhang L.; Jing X.; Li R.; Zhu S.; Gao H.; Fang J.; Xia Q. Chin. J. Org. Chem. 2014, 34, 1523. (in Chinese)
[10]
刘雨燕, 方烨汶, 张莉, 金小平, 李瑞丰, 朱帅汝, 高浩其, 房江华, 夏勤波, 有机化学, 2014, 34, 1523.).
[11]
Tseng C.C.; Paisley S.D.; Goering H.L. J. Org. Chem. 1986, 51, 2884.
[12]
Pérez M.; Fa?anás-Mastral M.; Bos P.H.; Rudolph A.; Haru- tyunyan S.R.; Feringa B.L. Nat. Chem. 2011, 3, 377.
[13]
(a) Persson E. S. M.; Klaveren M.V.; Grove D.M.; B?ckvall J.E.; Koten G.V. Chem. Eur. J. 1995, 1, 351.
[13]
(b) Bertz S.H.; Cope S.; Murphy M.; Ogle C.A.; Taylor B.J. J. Am. Chem. Soc. 2007, 129, 7208.
[14]
(a) Bartholomew E.R.; Bertz S.H.; Cope S.; Murphy M.; Ogle C.A. J. Am. Chem. Soc. 2008, 130, 11244.
[14]
(b) Xu H.; Man Q.; Lin Y.; Li Y.; Feng Y. Chin. J. Org. Chem. 2010, 30, 9. (in Chinese)
[14]
许华建, 蔄秋石, 林义成, 李源源, 冯乙已, 有机化学, 2010, 30, 9.).
[15]
Nguyen T. N. T.; Thiel N.O.; Teichert J.F. Chem. Commun. 2017, 53, 11686.
[16]
Yang B.; Wang Z.-X. J. Org. Chem. 2017, 82, 4542.
[17]
Frlan R.; Sova M.; Gobec S.; Stavber G.; ?asar Z. J. Org. Chem. 2015, 80, 7803.
[18]
Franco T.D.; Epenoy A.; Hu X. Org. Lett. 2015, 17, 4910.
[19]
Kim H.J.; Su L.; Jung H.; Koo S. Org. Lett. 2011, 13, 2682.
[20]
Guo S.; Yuan Y.; Xiang J. New J. Chem. 2015, 39, 3093.
[21]
Zhu Z.-F.; Tu,. J-L.; Liu, F. Chem. Commun. 2019, 55, 11478.
[22]
Mayer M.; Czaplik W.M.; Jacobi von Wangelin, A.Adv. Synth. Catal. 2010, 352, 2147.
[23]
Tamaru Y.; Kagotani M.; Yoshida Z.-I. J. Chem. Soc., Chem. Commun. 1978, 8, 367.
[24]
Deng W.-H.; Ye F.; Bai X.-F.; Li L.; Song T.; Wei Y.-L.; Xu L.-W. RSC Adv. 2014, 4, 479.
[25]
Kobayashi Y.; Tokoro Y.; Watatani K. Eur. J. Org. Chem. 2000, 23, 3825.
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