Citation: Liu Zhou, Yi Jiuyin, Zhang Ying, Tao Chuanzhou, Zhang Zhicheng, Shi Ninghuan, Cheng Qingfang. (NHC)CuCl-Catalyzed Hydroboration of Symmetric Internal Alkynes[J]. Chemistry, ;2018, 81(5): 476-479. shu

(NHC)CuCl-Catalyzed Hydroboration of Symmetric Internal Alkynes

School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005

Corresponding author: Tao Chuanzhou, taocz@hhit.edu.cn Cheng Qingfang, spring817191@sina.com
Received Date: 22 December 2017
Accepted Date: 18 March 2018

Figures(3)

An efficient access to vinylboronates was achieved through (NHC)CuCl-catalyzed hydroboration of symmetric internal alkynes. With bis(pinacolato)diboron and symmetric internal alkynes as starting materials, single configuration of vinylboronates were obtained after protonation of vinylcopper, and their structure were all determined by ¹H NMR, ¹³C NMR and HRMS. The optimal reaction conditions were systematically screened. Based on the reaction investigation, the possible reaction mechanism was discussed. This highly practical hydroboration process, which can be carried out at mild conditions, enjoys operational simplicity, as well as environmental benign catalyst.
- (NHC)CuCl,
- Internal alkyne,
- Bis(pinacolato)diboron,
- Hydroboration,
- Vinylboronate
1. [1]
  N Miyaura, A Suzuki. Chem. Rev., 1995, 95:2457~2483.
2. [2]
  C Tao, Z Zhang, J Wu et al. Chin. Chem. Lett., 2014, 25:532~534.
3. [3]
  M Kuriyama, R Shimazawa, R Shirai. J. Org. Chem., 2008, 73:1597~1600.
4. [4]
  I Beletskaya, C Moberg. Chem. Rev., 2006, 106:2320~2354.
5. [5]
  L Song, T Wang, X Zhang et al. ACS Catal., 2017, 7:1181~1185.
6. [6]
  K Yuan, N Suzuki, S K Mellerup et al. Org. Lett., 2016, 18:720~723.
7. [7]
  W J Jang, W L Lee, J H Moon et al. Org. Lett., 2016, 18:1390~1393.
8. [8]
  S Krautwald, M J Bezdek, P J Chirik. J. Am. Chem. Soc., 2017, 139:3868~3875.
9. [9]
  T Fujihara, K Semba, J Terao et al. Catal. Sci. Technol., 2014, 4:1699~1709.
10. [10]
  H Yoshida, I Kageyuki, K Takaki. Org. Lett., 2014, 16:3512~3515.
11. [11]
  J E Lee, J Kwon, J Yun. Chem. Commun., 2008, 44:733~734.
12. [12]
  H Jang, A R Zhugralin, Y Lee et al. J. Am. Chem. Soc., 2011, 133:7859~7871.
13. [13]
  A L Moure, R G Arrayas, D J Cardenas et al. J. Am. Chem. Soc., 2012, 134:7219~7222.
14. [14]
  Y D Bidal, F Lazreg, C S J Cazin. ACS Catal., 2014, 4:1564~1569.
15. [15]
  H R Kim, J Yun. Chem. Commun., 2011, 47:2943~2945.
16. [16]
  W Yuan, S Ma. Org. Biomol. Chem., 2012, 10:7266~7268.
17. [17]
  M Hans, J Lorkowski, A Demonceau et al. Beilstein J. Org. Chem., 2015,11(1):2318~2325.
1. [1]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
2. [2]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
3. [3]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
4. [4]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
5. [5]
  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
6. [6]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
7. [7]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
8. [8]
  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
9. [9]
  Yinjie Xu , Suiqin Li , Lihao Liu , Jiahui He , Kai Li , Mengxin Wang , Shuying Zhao , Chun Li , Zhengbin Zhang , Xing Zhong , Jianguo Wang . Enhanced Electrocatalytic Oxidation of Sterols using the Synergistic Effect of NiFe-MOF and Aminoxyl Radicals. Acta Physico-Chimica Sinica, 2024, 40(3): 2305012-0. doi: 10.3866/PKU.WHXB202305012
10. [10]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
11. [11]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
12. [12]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
13. [13]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
14. [14]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
15. [15]
  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
16. [16]
  Yufan Pan , Xue Ding , Jiayu Lin , Haiting Wu , Hairong Huang , Cuixue Chen , Meiling Ye . Oil Cosmetics, Charming Chemistry: A Gradient Science Popularization Scheme for Cream Cosmetic Preparation. University Chemistry, 2025, 40(4): 382-389. doi: 10.12461/PKU.DXHX202406078
17. [17]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
18. [18]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
19. [19]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
20. [20]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177

Get Citation

PDF

XML

Metrics

PDF Downloads(15)
Abstract views(1674)
HTML views(511)

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