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

  • 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.
  • 加载中
    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. 

  • 加载中
    1. [1]

      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

    2. [2]

      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

    3. [3]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng 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

    4. [4]

      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

    5. [5]

      Zhenhuan WangWeifei WeiRuijie MaDou LuoZhanxiang ChenJun ZhangLiyang YuGang LiZhenghui 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

    6. [6]

      Dong XiangKunzhen LiKanghua MiaoRan LongYujie XiongXiongwu 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

    7. [7]

      Yajin LiHuimin LiuLan MaJiaxiong LiuDehua 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

    8. [8]

      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

    9. [9]

      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

    10. [10]

      Jie ZHAOSen LIUQikang YINXiaoqing LUZhaojie 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

    11. [11]

      Baitong Wei Rongxiu Zhu Zhenghu Xu . Thalidomide: Defeating the Three Evils. University Chemistry, 2026, 41(2): 273-278. doi: 10.12461/PKU.DXHX202502020

    12. [12]

      Dongheng WANGSi LIShuangquan 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

    13. [13]

      Lin LIJiaxue LIMeixia YANGJiayu DINGJiaqi JINGRuiping ZHANG . Preparation of mitoxantrone self-assembled carrier-free nanodrugs regulated by sodium acetate for apoptosis induction of human breast carcinoma cells. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2536-2548. doi: 10.11862/CJIC.20250138

    14. [14]

      Ruitong Zhang Zhiqiang Zeng Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004

    15. [15]

      Chen LUQinlong HONGHaixia ZHANGJian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407

    16. [16]

      Hongting Yan Aili Feng Rongxiu Zhu Lei Liu Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

    17. [17]

      Lancanghong Chen Xingtai Yu Tianlei Zhao Qizhi Yao . Exploration of Abnormal Phenomena in Iodometric Copper Quantitation Experiment. University Chemistry, 2025, 40(7): 315-320. doi: 10.12461/PKU.DXHX202408089

    18. [18]

      Huasen LuShixu SongQisen JiaGuangbo LiuLuhua Jiang . Advances in Cu2O-based Photocathodes for Photoelectrochemical Water Splitting. Acta Physico-Chimica Sinica, 2024, 40(2): 2304035-0. doi: 10.3866/PKU.WHXB202304035

    19. [19]

      Zhengyu ZhouHuiqin YaoYoulin WuTeng LiNoritatsu TsubakiZhiliang 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]

      Xiuyun Wang Jiashuo Cheng Yiming Wang Haoyu Wu Yan Su Yuzhuo Gao Xiaoyu Liu Mingyu Zhao Chunyan Wang Miao Cui Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067

Metrics
  • PDF Downloads(0)
  • Abstract views(1547)
  • HTML views(375)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return