Citation: Ma Nan, Zeng Xianghua. Cu2O-Catalyzed Green Oxidative Terminal Alkynes Homocoupling without Bases[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1556-1561. doi: 10.6023/cjoc201712038 shu

Cu2O-Catalyzed Green Oxidative Terminal Alkynes Homocoupling without Bases

  • Corresponding author: Zeng Xianghua, xianghuazeng@mail.zjxu.edu.cn
  • Received Date: 27 December 2017
    Revised Date: 31 January 2018
    Available Online: 11 June 2018

    Fund Project: the National Natural Science Foundation of Zhejiang Province LY17B030011Project supported by the National Natural Science Foundation of Zhejiang Province (No. LY17B030011) and the Jiaxing Science and Technology Project (No. 2015AY11014)the Jiaxing Science and Technology Project 2015AY11014

Figures(4)

  • A high efficient method for the synthesis of 1, 3-diynes derivatives which employed terminal alkynes as the substrates and copper(I) oxide as the catalyst was developed. This method possessed the character of base-free and mild reaction conditions. The reaction mechanism was also studied. Furthermore, this reaction could be magnified to gram scale and the catalyst of copper(I) oxide could be recycled.
  • 加载中
    1. [1]

      (a) Lerch, M. L. ; Harper, M. K. ; Faulkner, D. J. J. Nat. Prod. 2003, 66, 667.
      (b) Lechner, D. ; Stavri, M. ; Oluwatuyi, M. ; Perda-Miranda, R. ; Gibbons, S. Phytochemistry 2004, 65, 331.
      (c) Constable, C. P. ; Towers, G. H. N. Planta Med. 1989, 55, 35.
      (d) Zhou, Y. Z. ; Ma, H. Y. ; Chen, H. ; Qiao, L. ; Yao, Y. ; Cao, J. Q. ; Pei, Y. H. Chem. Pharm. Bull. 2006, 54, 1455.
      (e) Ladika, M. ; Fisk, T. E. ; Wu, W. W. ; Jons, S. D. J. Am. Chem. Soc. 1994, 116, 12093.
      (f) Mayer, S. F. ; Steinreiber, A. ; Orru, R. V. A. ; Faber, K. J. Org. Chem. 2002, 67, 9115.
      (g) Zeni, G. ; Panatieri, R. B. ; Lissner, E. ; Menezes, P. H. ; Braga, A. L. ; Stefani, H. A. Org. Lett. 2001, 3, 819.
      (h) Stüts, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320.

    2. [2]

      (a) Gholami, M. ; Tykwinski, R. R. Chem. Rev. 2006, 106, 4997.
      (b) Baxter, P. N. W. ; Dali-Youcef, R. J. Org. Chem. 2005, 70, 4935.
      (c) Marsden, J. A. ; Haley, M. M. J. Org. Chem. 2005, 70, 10213.

    3. [3]

      (a) Cataldo, F. In Polyynes: Synthesis Properties, and Applications, CRC Press/Taylor & Francis, Boca Raton, Florida, 2005.
      (b) Diederich, F. ; Stang, P. J. ; Tykwinski, R. R. Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2005.

    4. [4]

      Crowley, J. D.; Goldup, S. M.; Lee, A. L.; Leigh, D. A.; McBurney, R. T. Chem.Soc.Rev. 2009, 38, 1530.  doi: 10.1039/b804243h

    5. [5]

      Glaser, C. Ber.Dtsch.Chem.Ges. 1869, 2, 422.  doi: 10.1002/(ISSN)1099-0682

    6. [6]

      Chen, L.; Lemma, B. E.; Rich, J. S.; Mack, J. Green Chem. 2014, 16, 1101.  doi: 10.1039/C3GC41847B

    7. [7]

      Mo, G.; Tian, Z.; Li, J.; Wen, G.; Yang, X. Appl. Organomet.Chem. 2015, 29, 231.  doi: 10.1002/aoc.v29.4

    8. [8]

      (a) Leyva-Pérez, A. ; Doménech, A. ; Al-Resayes, S. I. ; Corma, A. ACS Catal. 2012, 2, 121.
      (b) Peng, H. ; Xi, Y. ; Ronaghi, N. ; Dong, B. ; Akhmedov, G. N. ; Shi, X. J. Am. Chem. Soc. 2014, 136, 13174.

    9. [9]

      (a) Fan, X. ; Li, N. ; Shen, T. ; Cui, X. -M. ; Lv, H. ; Zhu, H. -B. ; Guan, Y. -H. Tetrahedron 2014, 70, 256.
      (b) Yin, K. ; Li, C. -J. ; Li, J. ; Jia, X. -S. Appl. Organomet. Chem. 2011, 25, 16.
      (c) Navale, B. S. ; Bhat, R. G. RSC Adv. 2013, 3, 5220.
      (d) Zhang, S. ; Liu, X. ; Wang, T. Adv. Synth. Catal. 2011, 353, 1463.
      (e) Jia, X. ; Yin, K. ; Li, C. ; Li, J. ; Bian, H. Green Chem. 2011, 13, 2175.
      (f) Balaraman, K. ; Kesavan, V. Synthesis 2010, 3461.
      (g) Kusuda, A. ; Xu, X. -F. ; Wang, X. ; Tokunaga, E. ; Shibata, N. Green Chem. 2011, 13, 843.
      (h) Adimurthy, S. ; Malakar, C. C. ; Beifuss, U. J. Org. Chem. 2009, 74, 5648.
      (i) Yin, K. ; Li, C. ; Li, J. ; Jia, X. Green Chem. 2011, 13, 591.
      (j) Wang, D. ; Li, J. ; Li, N. ; Gao, T. ; Hou, S. ; Chen, B. Green Chem. 2010, 12, 45.
      (k) Kabalka, G. W. ; Wang, L. ; Pagni, R. M. Synlett 2001, 108.
      (l) Li, Y. -N. ; Wang, J. -L. ; He, L. -N. Tetrahedron Lett. 2011, 52, 3485.
      (m) Sagadevan, A. ; Charpe, V. P. ; Hwang, K. C. Catal. Sci. Technol. 2016, 6, 7688.
      (n)Sagadevan, A. ; Lyu, P. -C. ; Hwang, K. C. Green Chem. 2016, 18, 4526.
      (o) Oishi, T. ; Katayama, T. ; Yamaguchi, K. ; Mizuno, N. Chem. Eur. J. 2009, 15, 7539.
      (p) Oishi, T. ; Yamaguchi, K. ; Mizuno, N. ACS Catal. 2011, 1, 1351.
      (q) Zhu, Y. ; Shi, Y. Org. Biomol. Chem. 2013, 11, 7451.
      (r) Kamata, K. ; Yamaguchi, S. ; Kotani, M. ; Yamaguchi, K. ; Mizuno, N. Angew. Chem., Int. Ed. 2008, 47, 2407.

    10. [10]

      Allen, S. E.; Walvoord, R. R.; Padilla-Salinas, R.; Kozlowski, M. C. Chem.Rev. 2013, 113, 6234.  doi: 10.1021/cr300527g

    11. [11]

      Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org.Lett. 2009, 11, 709.  doi: 10.1021/ol8027863

    12. [12]

      Ye, R.; Zhukhovitskiy, A. V.; Deraedt, C. V.; Toste, F. D.; Somorjai, G. A. Acc.Chem.Res. 2017, 50, 1894.  doi: 10.1021/acs.accounts.7b00232

    13. [13]

      Tang, B.-X.; Fang, X.-N.; Kuang, R.-Y.; Wu, J.-H.; Chen, Q.; Hu, S.-J.; Liu, Y.-L. Appl.Organomet.Chem. 2016, 30, 943.  doi: 10.1002/aoc.v30.11

    14. [14]

      Su, L.; Dong, J.; Liu, H.; Sun, M.; Qiu, R.; Zhou, Y.; Yin, S.-F. J. Am.Chem.Soc. 2016, 138, 12348.  doi: 10.1021/jacs.6b07984

    15. [15]

      Xu, H.; Wu, K.; Tian, J.; Zhu, L.; Yao, X. Green Chem. 2018, 20, 793.  doi: 10.1039/C7GC03120C

    16. [16]

      Theunissen, C.; Evano, G. Org.Lett. 2014, 16, 4488.  doi: 10.1021/ol502030y

    17. [17]

      Chinchilla, R.; Najera, C. Chem.Soc.Rev. 2011, 40, 5084.  doi: 10.1039/c1cs15071e

  • 加载中
    1. [1]

      Huasen Lu , Shixu Song , Qisen Jia , Guangbo Liu , Luhua Jiang . Advances in Cu2O-based Photocathodes for Photoelectrochemical Water Splitting. Acta Physico-Chimica Sinica, 2024, 40(2): 2304035-0. doi: 10.3866/PKU.WHXB202304035

    2. [2]

      Qiang ZHAO , Zhinan GUO , Shuying LI , Junli WANG , Zuopeng LI , Zhifang JIA , Kewei WANG , Yong GUO . Cu2O/Bi2MoO6 Z-type heterojunction: Construction and photocatalytic degradation properties. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 885-894. doi: 10.11862/CJIC.20230435

    3. [3]

      Simin Fang ,  Wei Huang ,  Guanghua Yu ,  Cong Wei ,  Mingli Gao ,  Guangshui Li ,  Hongjun Tian ,  Wan Li . Integrating Science and Education in a Comprehensive Chemistry Design Experiment: The Preparation of Copper(I) Oxide Nanoparticles and Its Application in Dye Water Remediation. University Chemistry, 2024, 39(8): 282-289. doi: 10.3866/PKU.DXHX202401023

    4. [4]

      Kaihui Huang , Dejun Chen , Xin Zhang , Rongchen Shen , Peng Zhang , Difa Xu , Xin Li . Constructing Covalent Triazine Frameworks/N-Doped Carbon-Coated Cu2O S-Scheme Heterojunctions for Boosting Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(12): 2407020-0. doi: 10.3866/PKU.WHXB202407020

    5. [5]

      Qu ZHANG , Tao WANG , Yinying WANG , Bo LI , Dongling WU . Synthesis of amino acid-functionalized nitrogen-doped carbon dots/cuprous oxidecomposite material and its performance in aqueous zinc-ion batteries. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 488-498. doi: 10.11862/CJIC.20250272

    6. [6]

      Lili Jiang ,  Shaoyu Zheng ,  Xuejiao Liu ,  Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004

    7. [7]

      Meng Lin ,  Hanrui Chen ,  Congcong Xu . Preparation and Study of Photo-Enhanced Electrocatalytic Oxygen Evolution Performance of ZIF-67/Copper(I) Oxide Composite: A Recommended Comprehensive Physical Chemistry Experiment. University Chemistry, 2024, 39(4): 163-168. doi: 10.3866/PKU.DXHX202308117

    8. [8]

      Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144

    9. [9]

      Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn2S4 photocatalyst for H2O2 production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064

    10. [10]

      Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073

    11. [11]

      Huilin ZHENG , Tao WANG , Ruilin GAO , Mengke ZHOU , Xinyue LI , Hui WANG , Xiaoxia GU . Antitumor and antibacterial activities of transition metal complexes incorporating pyridyl salicylaldehyde Schiff base. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 897-905. doi: 10.11862/CJIC.20250358

    12. [12]

      Zhang Xiaofei ,  Xu Shanhao ,  Wang Zhiyuan ,  He Long ,  Huang Tangcheng ,  Xu Yongming ,  Bian Yucui ,  Li Yike ,  Chen Haijun ,  Li Zhongjun . Surface doping of graphene into BiOCl for efficient photocatalytic amine coupling under visible light. Acta Physico-Chimica Sinica, 2026, 42(5): 100202-. doi: 10.1016/j.actphy.2025.100202

    13. [13]

      Xingyu Wang ,  Xijia Ren ,  Yulu Zhang ,  Yuewei Yang ,  Jingyan Yi ,  Yuan Li ,  Kai Guo . G蛋白偶联受体的生命叙事:从信号密码到健康卫士. University Chemistry, 2026, 41(10): 182-189. doi: 10.12461/PKU.DXHX202509101

    14. [14]

      Zixuan Zhao ,  Miao Fan . “Carbon” with No “Ester”: A Boundless Journey of CO2 Transformation. University Chemistry, 2025, 40(7): 213-217. doi: 10.12461/PKU.DXHX202409040

    15. [15]

      Chaolin Mi , Yuying Qin , Xinli Huang , Yijie Luo , Zhiwei Zhang , Chengxiang Wang , Yuanchang Shi , Longwei Yin , Rutao Wang . Galvanic Replacement Synthesis of Graphene Coupled Amorphous Antimony Nanoparticles for High-Performance Sodium-Ion Capacitor. Acta Physico-Chimica Sinica, 2024, 40(5): 2306011-0. doi: 10.3866/PKU.WHXB202306011

    16. [16]

      Senqiang Zhu ,  Ruohan Li ,  Yujia Yang ,  Jinzhi Liao ,  Rui Liu . 聚光成辉——Suzuki偶联反应高效制备聚集诱导发射荧光分子及其潜指纹识别应用. University Chemistry, 2026, 41(5): 109-119. doi: 10.12461/PKU.DXHX202511066

    17. [17]

      Yajun Hou ,  Jinxin Liu ,  Tao Chen ,  Yi Zhang ,  Lei Zhou . Sonogashira coupling reaction in ionic liquids: a detailed exploration of experiment 4.4D in the “101 Plan” synthetic chemistry curriculum. University Chemistry, 2026, 41(6): 136-144. doi: 10.12461/PKU.DXHX202510101

    18. [18]

      Wen WANG , Ying XU , Gang XIONG , Lixin YOU , Yaguang SUN . Pd-NHC-functionalized La-metal-organic framework for efficient Suzuki-Miyaura cross-coupling reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1475-1484. doi: 10.11862/CJIC.20260025

    19. [19]

      Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129

    20. [20]

      Zimo Shen ,  Tongwei Zhang ,  Zhiyi Zhu ,  Zonghao Gong ,  Qing Feng ,  Jinyi Yang ,  Zhen Li ,  Min Liu ,  Wei Qi . From Alkaloid to Anticancer Agent: The Transformative Journey of Camptothecin. University Chemistry, 2025, 40(10): 161-165. doi: 10.12461/PKU.DXHX202411027

Metrics
  • PDF Downloads(31)
  • Abstract views(2487)
  • HTML views(414)

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