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

doi:10.6023/cjoc202008012

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 695-701.DOI: 10.6023/cjoc202008012 Previous Articles Next Articles

Article

铜催化芳基(或烷基)卤化物选择性烯丙基化反应研究

韩博士^a, 时郑^a, 何慧红^a^,^*(), 张兴华^a^,^b^,^*()

a 上海应用技术大学化学与环境工程学院上海 201418
b 宁波大学新药技术研究院浙江宁波 315211

收稿日期:2020-08-10 修回日期:2020-09-17 发布日期:2020-10-15
通讯作者: 何慧红, 张兴华
作者简介:
* Corresponding authors. E-mail: xhzhang@sit.edu.cn; eilynn1207@126.com
基金资助:
国家自然科学基金(21871182)

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

Boshi Han^a, Zheng Shi^a, Huihong He^a^,^*(), Xinghua Zhang^a^,^b^,^*()

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:2020-08-10 Revised:2020-09-17 Published:2020-10-15
Contact: Huihong He, Xinghua Zhang
Supported by:
the National Natural Science Foundation of China(21871182)

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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.

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Fig. & Tab. 5

References 25

[1]	(a) Zhang Z.-Q.; Zhang B.; Lu X.; Liu J.-H.; Lu X.-Y.; Xiao B.; Fu Y. Org. Lett. 2016, 18, 952. doi: 10.1021/acs.orglett.5b03692
	(b) Nguyen T. N. T.; Thiel N.O.; Pape F.; Teichert J.F. Org. Lett. 2016, 18, 2455. doi: 10.1021/acs.orglett.6b00941
	(c) Xu G.; Zhao H.; Fu B.; Cang A.; Zhang G.; Xiong T.; Zhang Q. Angew. Chem. Int. Ed. 2017, 56, 13130. doi: 10.1002/anie.201707070
[2]	(a) Trost B.M.; Van Vranken, D.L.Chem. Rev. 1996, 96, 395. doi: 10.1021/cr9409804 pmid: F55E7FAC-BD05-4F88-8B90-D9B20F330844
	(b) Falciola C.A.; Alexakis A. Eur. J. Org. Chem. 2008, 22, 3765. pmid: F55E7FAC-BD05-4F88-8B90-D9B20F330844
	(c) Cui P.; Liu H.; Zhang D.; Wang C. Chin. J. Org. Chem. 2012, 32, 1401. (in Chinese) doi: 10.6023/cjoc1110071 pmid: F55E7FAC-BD05-4F88-8B90-D9B20F330844
	崔朋雷, 刘海燕, 张冬暖, 王春, 有机化学, 2012, 32, 1401.). doi: 10.6023/cjoc1110071 pmid: F55E7FAC-BD05-4F88-8B90-D9B20F330844
	(d) Deng Y.; Yang W.; Yang X.; Yang D. Chin. J. Org. Chem. 2017, 37, 3039. (in Chinese) doi: 10.6023/cjoc201704034 pmid: F55E7FAC-BD05-4F88-8B90-D9B20F330844
	邓颖颖, 杨文, 杨新, 杨定乔, 有机化学, 2017, 37, 3039.). doi: 10.6023/cjoc201704034 pmid: F55E7FAC-BD05-4F88-8B90-D9B20F330844
	(e) Zhang H.; Gu Q.; You S. Chin. J. Org. Chem. 2019, 39, 15. (in Chinese) pmid: F55E7FAC-BD05-4F88-8B90-D9B20F330844
	张慧君, 顾庆, 游书力, 有机化学, 2019, 39, 15.). doi: 10.6023/cjoc201809037 pmid: F55E7FAC-BD05-4F88-8B90-D9B20F330844
[3]	(a) Han X.; Zhang Y.; Wu J. J. Am. Chem. Soc. 2010, 132, 4104. doi: 10.1021/ja100747n
	(b) Lauer A.M.; Mahmud F.; Wu J. J. Am. Chem. Soc. 2011, 133, 9119. doi: 10.1021/ja202954b
	(c) Hornillos V.; Pérez M.; Fañanás-Mastral M.; Feringa B.L. J. Am. Chem. Soc. 2013, 135, 2140. doi: 10.1021/ja312487r
	(d) Magrez M.; Guen Y.L.; Baslé O.; Crévisy C.; Mauduit M. Chem. Eur. J. 2013, 19, 1199. doi: 10.1002/chem.201203969
[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. doi: 10.1002/chem.v20.47
[5]	(a) Li Z.; Sun H.-M.; Shen Q. Org. Biomol. Chem. 2016, 14, 3314. doi: 10.1039/C6OB00247A
	(b) Zhang J.; Lu G.; Xu J.; Sun H.; Shen Q. Org. Lett. 2016, 18, 2860. doi: 10.1021/acs.orglett.6b01134
[6]	(a) Czaplik W.M.; Mayer M.; Jacobi von Wangelin, A.Angew. Chem. Int. Ed. 2009, 48, 607. doi: 10.1002/anie.v48:3
	(b) Mayer M.; Czaplik W.M.; Jacobi von Wangelin, A.Adv. Synth. Catal. 2010, 352, 2147. doi: 10.1002/adsc.201000228
[7]	(a) Cui X.; Wang S.; Zhang Y.; Deng W.; Qian Q.; Gong H. Org. Biomol. Chem. 2013, 11, 3094. doi: 10.1039/c3ob40232k
	(b) Chen H.; Jia X.; Yu Y.; Gong H. Angew. Chem. Int. Ed. 2017, 56, 13103. doi: 10.1002/anie.201705521
[8]	Anka-Lufford L.L.; Prinsell M.R.; Weix D.J. J. Org. Chem. 2012, 77, 9989. doi: 10.1021/jo302086g
[9]	Qian X.; Auffrant A.; Felouat A.; Gosmini C. Angew. Chem. Int. Ed. 2011, 50, 10402. doi: 10.1002/anie.201104390
[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) doi: 10.6023/cjoc201403003 pmid: 3C7E234D-71D0-4A95-8A34-41864A84A8FB
	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.). doi: 10.6023/cjoc201403003 pmid: 3C7E234D-71D0-4A95-8A34-41864A84A8FB
[11]	Tseng C.C.; Paisley S.D.; Goering H.L. J. Org. Chem. 1986, 51, 2884. doi: 10.1021/jo00365a006
[12]	Pérez M.; Fañanás-Mastral M.; Bos P.H.; Rudolph A.; Haru- tyunyan S.R.; Feringa B.L. Nat. Chem. 2011, 3, 377. doi: 10.1038/nchem.1009
[13]	(a) Persson E. S. M.; Klaveren M.V.; Grove D.M.; Bäckvall J.E.; Koten G.V. Chem. Eur. J. 1995, 1, 351. doi: 10.1002/(ISSN)1521-3765
	(b) Bertz S.H.; Cope S.; Murphy M.; Ogle C.A.; Taylor B.J. J. Am. Chem. Soc. 2007, 129, 7208. doi: 10.1021/ja067533d
[14]	(a) Bartholomew E.R.; Bertz S.H.; Cope S.; Murphy M.; Ogle C.A. J. Am. Chem. Soc. 2008, 130, 11244. doi: 10.1021/ja801186c pmid: 2358A1E3-B1B1-44AF-9059-24E79D5FE43E
	(b) Xu H.; Man Q.; Lin Y.; Li Y.; Feng Y. Chin. J. Org. Chem. 2010, 30, 9. (in Chinese) pmid: 2358A1E3-B1B1-44AF-9059-24E79D5FE43E
	许华建, 蔄秋石, 林义成, 李源源, 冯乙已, 有机化学, 2010, 30, 9.). pmid: 2358A1E3-B1B1-44AF-9059-24E79D5FE43E
[15]	Nguyen T. N. T.; Thiel N.O.; Teichert J.F. Chem. Commun. 2017, 53, 11686. doi: 10.1039/C7CC07008J
[16]	Yang B.; Wang Z.-X. J. Org. Chem. 2017, 82, 4542. doi: 10.1021/acs.joc.6b02564
[17]	Frlan R.; Sova M.; Gobec S.; Stavber G.; Časar Z. J. Org. Chem. 2015, 80, 7803. doi: 10.1021/acs.joc.5b01156
[18]	Franco T.D.; Epenoy A.; Hu X. Org. Lett. 2015, 17, 4910. doi: 10.1021/acs.orglett.5b02482
[19]	Kim H.J.; Su L.; Jung H.; Koo S. Org. Lett. 2011, 13, 2682. doi: 10.1021/ol200779y
[20]	Guo S.; Yuan Y.; Xiang J. New J. Chem. 2015, 39, 3093. doi: 10.1039/C4NJ02416H
[21]	Zhu Z.-F.; Tu,. J-L.; Liu, F. Chem. Commun. 2019, 55, 11478. doi: 10.1039/C9CC05385A
[22]	Mayer M.; Czaplik W.M.; Jacobi von Wangelin, A.Adv. Synth. Catal. 2010, 352, 2147. doi: 10.1002/adsc.201000228
[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. doi: 10.1039/C3RA44742A
[25]	Kobayashi Y.; Tokoro Y.; Watatani K. Eur. J. Org. Chem. 2000, 23, 3825.

Entry	Cat.	Ligand	Additive	T/℃	Yield^b/% of 3a/4a
1	CuSCN	PPh₃	LiCl	30	68/11
2	CuI	PPh₃	LiCl	30	70/11
3	CuCl	PPh₃	LiCl	30	61/12
4	CuBr	PPh₃	LiCl	30	74/10
5	CuBr	1,10-Phen	LiCl	30	66/7
6	CuBr	TMEDA	LiCl	30	N.R.
7	CuBr	DPPM	LiCl	30	59/9
8	CuBr	PCy₃	LiCl	30	74/12
9	CuBr	PPh₃	—	30	66/12
10	CuBr	PPh₃	LiBr	30	78/14
11^c	CuBr	PPh₃	LiBr	30	N.R.
12^d	CuBr	PPh₃	LiBr	30	N.R.
13	CuBr	PPh₃	LiBr	0	75/16
14	CuBr	PPh₃	LiBr	60	80/6
15	CuBr	PPh₃	LiBr	80	86/3(86)^e

Entry	Cat.	Ligand	Additive	T/℃	Yield^b/% of 3a/4a
1	CuSCN	PPh₃	LiCl	30	68/11
2	CuI	PPh₃	LiCl	30	70/11
3	CuCl	PPh₃	LiCl	30	61/12
4	CuBr	PPh₃	LiCl	30	74/10
5	CuBr	1,10-Phen	LiCl	30	66/7
6	CuBr	TMEDA	LiCl	30	N.R.
7	CuBr	DPPM	LiCl	30	59/9
8	CuBr	PCy₃	LiCl	30	74/12
9	CuBr	PPh₃	—	30	66/12
10	CuBr	PPh₃	LiBr	30	78/14
11^c	CuBr	PPh₃	LiBr	30	N.R.
12^d	CuBr	PPh₃	LiBr	30	N.R.
13	CuBr	PPh₃	LiBr	0	75/16
14	CuBr	PPh₃	LiBr	60	80/6
15	CuBr	PPh₃	LiBr	80	86/3(86)^e

铜催化芳基(或烷基)卤化物选择性烯丙基化反应研究

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

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