Copper-catalyzed Markovnikov hydroboration of aliphatic terminal alkenes using carbonyl as a weak directing group

被引:1
|
作者
Feng, Cancan [1 ]
Tang, Luqing [1 ]
Yang, Fan [1 ]
Wu, Yangjie [1 ]
机构
[1] Zhengzhou Univ, Key Lab Appl Chem Henan Univ, Coll Chem, Green Catalysis Ctr,Henan Key Lab Chem Biol & Orga, Zhengzhou 450052, Peoples R China
基金
中国国家自然科学基金;
关键词
SELECTIVE HYDROBORATION; ASYMMETRIC HYDROFUNCTIONALIZATION; FUNCTIONALIZATION; OLEFINS; HYDROAMINATION; BORYLATION;
D O I
10.1039/d3qo00988b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we reported a copper-catalyzed carbonyl-assisted hydroboration of terminal aliphatic alkenes with Markovnikov regioselectivity, employing easily available and stable B(2)Pin(2) as the boron source. This reaction proceeded smoothly with exclusive Markovnikov regioselectivity and provided facile access to a series of branched secondary alkyl boronic esters in moderate to excellent yields. The hydrogen source stemmed from the solvent, which was illustrated by the deuterium experiments.
引用
收藏
页码:4692 / 4697
页数:6
相关论文
共 33 条
  • [21] Copper-Catalyzed Regioselective C-H Aerobic Oxidative Cycloetherification of o-Arylphenols Bearing an Additional Directing Group
    Zhao, Jiaji
    Wang, Yong
    Zhu, Qiang
    SYNTHESIS-STUTTGART, 2012, 44 (10): : 1551 - 1555
  • [22] α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C-H activation: a safe carbene precursor and a weak directing group
    Singh, Anurag
    Kumar, Shreemoyee
    Volla, Chandra M. R.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (05) : 879 - 909
  • [23] A directing group switch in copper-catalyzed electrophilic C-H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole
    Begam, Hasina Mamataj
    Nandi, Shantanu
    Jana, Ranjan
    CHEMICAL SCIENCE, 2022, 13 (19) : 5726 - 5733
  • [24] Copper-catalyzed reductive amination of aromatic and aliphatic ketones with anilines using environmental-friendly molecular hydrogen
    Werkmeister, Svenja
    Junge, Kathrin
    Beller, Matthias
    GREEN CHEMISTRY, 2012, 14 (09) : 2371 - 2374
  • [25] Copper-catalyzed ortho C-H Azidation of Anilines Using Molecular Oxygen as Terminal Oxidant
    Lin Fengguirong
    Liang Yujie
    Li Xinyao
    Song Song
    Jiao Ning
    ACTA CHIMICA SINICA, 2019, 77 (09) : 906 - 910
  • [26] Palladium/Iron-Catalyzed Wacker-Type Oxidation of Aliphatic Terminal and Internal Alkenes Using O2
    Miyazaki, Mayu
    Ura, Yasuyuki
    ACS OMEGA, 2023, 8 (44): : 41983 - 41990
  • [27] Copper-catalyzed monochloromethylazidation to access transformable terminal alkyl chlorides using stoichiometric BrCH2Cl
    Zhang, Ya-Xuan
    Bian, Kang-Jie
    Jin, Ruo-Xing
    Yang, Chi
    Wang, Xi-Sheng
    CHEMICAL COMMUNICATIONS, 2021, 57 (46) : 5666 - 5669
  • [28] Copper-Catalyzed Chelation-Assisted ortho-Nitration of 2-Aryls Using Pharmacophoric Benzothiazoles and Benzoxazoles as Directing Groups
    Vinayak, Botla
    Ashok, Akudari
    Chandrasekharam, Malapaka
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (47) : 7127 - 7132
  • [29] Copper-Catalyzed Triboration of Terminal Alkynes Using B2pin2: Efficient Synthesis of 1,1,2-Triborylalkenes
    Liu, Xiaocui
    Ming, Wenbo
    Friedrich, Alexandra
    Kerner, Florian
    Marder, Todd B.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (01) : 304 - 309
  • [30] Copper-Catalyzed Direct Alkynylation of Electron-Deficient Polyfluoroarenes with Terminal Alkynes Using O2 as an Oxidant
    Wei, Ye
    Zhao, Huaiqing
    Kan, Jian
    Su, Weiping
    Hong, Maochun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) : 2522 - +