Citation: Hu Dongyan, Li Mengsun. Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)₂[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1926-1931. doi: 10.6023/cjoc201603003 shu

Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)₂

Hu Dongyan ^a,b,*,, ,
Li Mengsun ^a,b

a.
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041
b.
University of the Chinese Academy of Sciences, Beijing 100049

Corresponding author: Hu Dongyan, hudy@cib.ac.cn
Received Date: 3 March 2016
Revised Date: 11 April 2016

Figures(2)

In the presence of iodobenzene diacetate (PhI(OAc)₂), a new CuBr catalyzed coupling reaction of alkynes and amines for the synthesis of propargyl amines was developed. When terminal alkynes, PhI(OAc)₂, and amines were reacted in CH₃CN at 70 ℃ for 3 h under N₂ atmosphere and in the presence of CuBr, the desired propargyl amines were obtained in good yields. Furthermore, no matter aromatic or aliphatic alkynes, were all found to tolerate the reaction conditions. To the best of our knowledge, it is the first time that PhI(OAc)₂ has been used for the synthesis of propargyl amines in one-pot operation from alkynes and amines.
- cuprous bromide,
- PhI(OAc)₂,
- propargyl amines
1. [1]
  Ohno, H.; Ohta, Y.; Oishi, S.; Fujii, N. Angew. Chem., Int. Ed. 2007, 46, 2295. (b) Yan, B.; Liu, Y. Org. Lett. 2007, 9, 4323. (c) Zhang, X.; Corma, A. Angew. Chem., Int. Ed. 2008, 47, 4358. (d) Cao, K.; Zhang, F. M.; Tu, Y. Q.; Zhuo, X. T.; Fan, C. A. Chem. Eur. J. 2009, 15, 6332. (e) Ohta, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2009, 11, 1979. (f) Nakamura, H.; Onagi, S.; Kamakura, T. J. Org. Chem. 2005, 70, 2357. (g) Sugiishi, T.; Kimura, A.; Nakamura, H. J. Am. Chem. Soc. 2010, 132, 5332. (h) Nakamura, H.; Kamakura, T.; Ishikura, M.; Biellmann, J. F. J. Am. Chem. Soc. 2004, 126, 5958.
2. [2]
  Farwick, A.; Helmchen, G. Org. Lett. 2010, 12, 1108. (b) Jiang, B.; Xu, M. Angew. Chem., Int. Ed. 2004, 43, 2543. (c) Yoon, T.; Shair, M. D.; Danishefsky, S. J.; Shulteo, G. K. J. Org. Chem. 1994, 59, 3752.
3. [3]
  Giles, R. L.; Nkansah, R. A.; Looper, R. E. J. Org. Chem. 2010, 75, 261. (b) Samai, S.; Nandi, G. C.; Singh, M. S. Tetrahedron Lett. 2010, 51, 5555. (c) Nakamura, H.; Ishikura, M.; Sugiishi, T.; Kamakura, T.; Biellmann, J. F. Org. Biomol. Chem. 2008, 6, 1471. (d) Trybulski, E. J.; Zhang, J.; Kramss, R. H.; Mangano, R. M. J. Med. Chem. 1993, 36, 3533.
4. [4]
  Birkmayer, W.; Knol, J.; Riederer, P. J. Neural Transm. 1985, 64, 113. (b) Chen, J. J.; Swope, D. M.; Dashtipour, K. Clin. Ther. 2007, 29, 1825.
5. [5]
  Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968.
6. [6]
  Ahn, J. H.; Joung, M. J.; Yoon, N. M.; Oniciu, D. C.; Katritzky, A. R. J. Org. Chem. 1999, 64, 488.
7. [7]
  Bieber, L. W.; da Silva, M. F. Tetrahedron Lett. 2004, 45, 8281. (b) Fodor, A.; Kiss, A.; Debreczeni, N.; Hell, Z.; Gresits, I. Org. Biomol. Chem. 2010, 8, 4575. (c) Wei, C.; Li, C. J. J. Am. Chem. Soc. 2002, 124, 5683. (d) Shi, L.; Tu, Y. Q.; Wang, M.; Zhang, F. M.; Fan, C. A. Org. Lett. 2004, 6, 1001.
8. [8]
  Wei, C.; Li, Z.; Li, C. J. Org. Lett. 2003, 5, 4473.
9. [9]
  Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584. (b) Zhang, X.; Corma, A. Angew. Chem., Int. Ed. 2008, 47, 4358. (c) Chng, L. L.; Yang, J.; Wei Y.; Ying, J. Y. Adv. Synth. Catal. 2009, 351, 2887.
10. [10]
  Li, P. H.; Zhang, Y. C.; Wang, L. Chem. Eur. J. 2009, 15, 2045. (b) Zeng, T. Q.; Chen, W. W.; Li, C. J. Green Chem. 2010, 12, 570.
11. [11]
  Ramu, E.; Varala, R.; Sreelatha, N.; Adapaa, S. R. Tetrahedron Lett. 2007, 48, 7184.
12. [12]
  Zhang, Y.; Li, P.; Wang, M.; Wang, L. J. Org. Chem. 2009, 74, 4364. (b) Yadav, J. S.; Subba Reddy, B. V.; Hara Gopal, A. V.; Patil, K. S. Tetrahedron Lett. 2009, 50, 3493.
13. [13]
  Chen, W. W.; Bi, H. P.; Li, C. J. Synlett 2010, 475.
14. [14]
15. [15]
  Chen, X. L.; Chen, T. Q.; Zhou, Y. B.; Au, C. T.; Han, L. B.; Yin, S. F. Org. Biomol. Chem. 2014, 12, 247.
16. [16]
  Tang, Y. C.; Xiao, T. B.; Zhou, L. Tetrahedron Lett. 2012, 53, 6199.
17. [17]
  Rahman, M.; Bagdi, A. K.; Majee, A.; Hajra, A. Tetrahedron Lett. 2011, 52, 4437.
18. [18]
  Berrichi, A.; Bachir, R.; Benabdallah, M.; Choukchou-Braham, N. Tetrahedron Lett. 2015, 56, 1302.
19. [19]
  Park, K.; Heo, Y.; Lee, S. Org. Lett. 2013, 15, 3322.
20. [20]
  Kabalka, G. W.; Venkataiah, B.; Dong, G. Tetrahedron Lett. 2004, 45, 729.
21. [21]
  Fodor, A.; Kiss, A.; Debreczeni, N.; Hell, Z.; Gresits, I. Org. Biomol. Chem. 2010, 8, 4575.
1. [1]
  Jianfang QIN , Yuying ZHANG , Lijuan JIA , Jiaqi LIANG , Yuxing YANG , Haiying YANG , Xu LIU . Accurate determination of profenofos by Au_25-xAg_x(PET)₁₈ (PET=2-phenylethanethiol) nanocluster-based electrochemical sensors. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1164-1174. doi: 10.11862/CJIC.20250378
2. [2]
  Haozhe Huang , Pengjun Chen , Xiao Han , Junjie Bao . 基于产教融合的高分子化学实验改进探索——以苯丙乳液的合成与性能测试实验为例. University Chemistry, 2026, 41(5): 170-179. doi: 10.12461/PKU.DXHX202511160
3. [3]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
4. [4]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
5. [5]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
6. [6]
  Yinuo Wang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation. University Chemistry, 2025, 40(10): 208-216. doi: 10.12461/PKU.DXHX202411077
7. [7]
  Zhenhuan Wang , Weifei Wei , Ruijie Ma , Dou Luo , Zhanxiang Chen , Jun Zhang , Liyang Yu , Gang Li , Zhenghui Luo . 苯并[a]苯嗪受体的核心氰基化实现高效(19.04%)绿色溶剂加工的二元有机太阳能电池. Acta Physico-Chimica Sinica, 2026, 42(2): 100182-0. doi: 10.1016/j.actphy.2025.100182
8. [8]
  Ranhui Fu , Shixin Zhou , Ran Ji , Feifei Gao , Hui Xu . 季膦盐合成实验的改进与拓展——水相一步法合成乙基三苯基溴化膦及其力致发光锰配合物的制备及表征. University Chemistry, 2026, 41(5): 252-263. doi: 10.12461/PKU.DXHX202510018
9. [9]
  Dong Xiang , Kunzhen Li , Kanghua Miao , Ran Long , Yujie Xiong , Xiongwu Kang . Amine-Functionalized Copper Catalysts: Hydrogen Bonding Mediated Electrochemical CO₂ Reduction to C₂ Products and Superior Rechargeable Zn-CO₂ Battery Performance. Acta Physico-Chimica Sinica, 2024, 40(8): 2308027-0. doi: 10.3866/PKU.WHXB202308027
10. [10]
  Chunfang Zhang , Yuehua Liu , Lin Yang , Wenhui Xu , Mingtao Run , Cuimiao Zhang . 醋酸电离平衡常数测定实验的改进. University Chemistry, 2026, 41(5): 131-140. doi: 10.12461/PKU.DXHX202511002
11. [11]
  Tianrong Zhu , Fan Yu , Yuhang Liu , Haiyi Xu , Tingting Ma , Ming Li , Yuhang Xue , Yazhen Wang , Aihua Li , Biao Xiao , Xiaolun Peng . Intelligent Visualization, Precise Iodometry: Color Recognition-based Indirect Iodometric Method for Copper Determination. University Chemistry, 2026, 41(1): 264-275. doi: 10.12461/PKU.DXHX202503096
12. [12]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
13. [13]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
14. [14]
  Lin Ding , Jinpeng Zhang , Junfeng Li , Daying Liu . Color Catcher: A Marvelous Encounter of Starch and Iodine. University Chemistry, 2024, 39(6): 334-341. doi: 10.3866/PKU.DXHX202311064
15. [15]
  Yang Li , Yuxuan Zhang , Yuhai Tang , Lijuan Wang . Iodide anion-catalyzed green synthesis of m-cresol. University Chemistry, 2026, 41(7): 326-333. doi: 10.12461/PKU.DXHX202506054
16. [16]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
17. [17]
  Baitong Wei , Rongxiu Zhu , Zhenghu Xu . Thalidomide: Defeating the Three Evils. University Chemistry, 2026, 41(2): 273-278. doi: 10.12461/PKU.DXHX202502020
18. [18]
  Xinrong Wu , Yingying Ren , Jianxue Wang , Lijin Yang , Jia Jia , Nan Li , Na Zhao . 聚光捕胺——高灵敏胺响应型聚集诱导发光探针的合成及传感应用. University Chemistry, 2026, 41(5): 180-189. doi: 10.12461/PKU.DXHX202509129
19. [19]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-0. doi: 10.3866/PKU.WHXB202312010
20. [20]
  Jing Kang , Tianyuan Zhao , Qian Zhang , Zhiwen Zhang , Yanyuan Jia , Alideertu Dong . Spotlight on Chlorine: An Innovative Iodometric Method for Visualizing Residual Chlorine. University Chemistry, 2026, 41(3): 343-350. doi: 10.12461/PKU.DXHX202506050

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1903)
HTML views(431)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)2

Metrics

通讯作者: 陈斌, bchen63@163.com

Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)₂