Copper-catalyzed regioselective hydroboration of terminal alkynes in aqueous medium

被引:26
|
作者
Yao, Zi-Jian [1 ]
Hong, Shibin [1 ]
Zhang, Wei [1 ]
Liu, Mengyan [1 ]
Deng, Wei [1 ,2 ]
机构
[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 201418, Peoples R China
[2] Shanghai Univ, Nanosci & Technol Res Ctr, Shanghai 200444, Peoples R China
基金
美国国家科学基金会;
关键词
Catalysis; Regioselective; Hydroboration; Aqueous; Recyclable; BETA-CYCLODEXTRIN; DIBORON REAGENTS; METAL-COMPLEXES; CONSTRUCTION; ALKYLATION; LIGAND; ESTERS;
D O I
10.1016/j.tetlet.2016.01.049
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and environment-friendly copper-catalyzed hydroboration of terminal alkynes in aqueous medium was reported. Regioselectivity control was achieved in the presence of cyclodextrin-bispyridine ligand (CD-1). This protocol was successfully applied to inactivated terminal alkynes. Moreover, the ligand was recovered and reused without any loss of activity over five cycles. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:910 / 913
页数:4
相关论文
共 50 条
  • [1] Copper-Catalyzed Highly Regioselective Silylcupration of Terminal Alkynes to Form α-Vinylsilanes
    Wang, Peng
    Yeo, Xue-Liang
    Loh, Teck-Peng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) : 1254 - 1256
  • [2] Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes
    Barashkova, Xenia A.
    Parulava, Mikhail J.
    Kotovshchikov, Yury N.
    Latyshev, Gennadij V.
    Lukashev, Nikolay V.
    Beletskaya, Irina P.
    SYNTHESIS-STUTTGART, 2024, 56 (09): : 1498 - 1504
  • [3] Copper-Catalyzed Hydroalkylation of Terminal Alkynes
    Uehling, Mycah R.
    Suess, Alison M.
    Lalic, Gojko
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (04) : 1424 - 1427
  • [4] Copper-Catalyzed trans-Hydroboration of Terminal Aryl Alkynes: Stereodivergent Synthesis of Alkenylboron Compounds
    Jang, Won Jun
    Lee, Woo Lim
    Moon, Jong Hun
    Lee, Jin Yong
    Yun, Jaesook
    ORGANIC LETTERS, 2016, 18 (06) : 1390 - 1393
  • [5] Copper-catalyzed stereo- and regioselective hydrophosphorylation of terminal alkynes: scope and mechanistic study
    Li, Junchen
    Gao, Zhenhua
    Guo, Yongbiao
    Liu, Haibo
    Zhao, Peichao
    Bi, Xiaojing
    Shi, Enxue
    Xiao, Junhua
    RSC ADVANCES, 2022, 12 (29) : 18889 - 18896
  • [6] Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water
    da Costa, Jessie S.
    Braun, Roger K.
    Horn, Pedro A.
    Ludtke, Diogo S.
    Moro, Angelica V.
    RSC ADVANCES, 2016, 6 (65): : 59935 - 59938
  • [7] Copper-Catalyzed Decarboxylative Alkylation of Terminal Alkynes
    Ye, Changqing
    Li, Yajun
    Bao, Hongli
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (21) : 3720 - 3724
  • [8] Copper-Catalyzed Synthesis of 1,1-Diborylalkanes through Regioselective Dihydroboration of Terminal Alkynes
    Lee, Sumin
    Li, Dingxi
    Yun, Jaesook
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) : 2440 - 2443
  • [9] Regioselective and Enantioselective Copper-Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes
    Yuan, Yang
    Zhang, Youcan
    Li, Wenbo
    Zhao, Yanying
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (40)
  • [10] Copper-Catalyzed Regioselective Reaction of Internal Alkynes and Diaryliodonium Salts
    Xu, Ze-Feng
    Cai, Chen-Xin
    Liu, Jin-Tao
    ORGANIC LETTERS, 2013, 15 (09) : 2096 - 2099