4-Cyanopyridine-catalyzed anti-Markovnikov selective hydroboration of alkenes

被引：21
作者：
Xu, Rui [1 ]
Lu, Guo-ping [1 ]
Cai, Chun [1 ]
机构：
[1] Nanjing Univ Sci & Technol, Chem Engn Coll, 200 Xiao Ling Wei, Nanjing 210094, Jiangsu, Peoples R China
来源：
NEW JOURNAL OF CHEMISTRY | 2018年 / 42卷 / 20期
关键词：
CROSS-COUPLING REACTION; CATALYZED HYDROBORATION; ISOMERIZATION-HYDROBORATION; 1,1-DISUBSTITUTED ALKENES; COBALT CATALYSTS; VINYL ARENES; BORYLATION; HALIDES; ALKYNES; PINACOLBORANE;
D O I：
10.1039/c8nj03222j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly selective anti-Markovnikov hydroboration reaction of alkenes with bis(pinacolato)diboron catalyzed by 4-cyanopyridine has been described. This strategy provides an efficient, practical and environmentally benign protocol for the construction of alkylboronates in moderate to good yields under metal-free conditions. A radical mechanism proceeding via a 4-cyanopyridine-ligated boryl radical was proposed.
引用
收藏
页码：16456 / 16459
页数：4
相关论文
共 64 条
  • [1] Ang N. W. J., 2018, SYNTHESIS-STUTTGART, P803
  • [2] [Anonymous], 1975, ORGANIC SYNTHESES VI
  • [3] Iron-Catalyzed Borylation of Alkyl Electrophiles
    Atack, Thomas C.
    Lecker, Rachel M.
    Cook, Silas P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (27) : 9521 - 9523
  • [4] Bailly B A. F. L, 2012, CHEM COMMUN, V48, P1580
  • [5] Fe(III)/NaBH4-Mediated Free Radical Hydrofluorination of Unactivated Alkenes
    Barker, Timothy J.
    Boger, Dale L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13588 - 13591
  • [6] Aluminum-Catalyzed Hydroboration of Alkenes
    Bismuto, Alessandro
    Cowley, Michael J.
    Thomas, Stephen P.
    [J]. ACS CATALYSIS, 2018, 8 (03): : 2001 - 2005
  • [7] Asymmetric organocatalytic diboration of alkenes
    Bonet, Amadeu
    Sole, Cristina
    Gulyas, Henrik
    Fernandez, Elena
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (33) : 6621 - 6623
  • [8] Metal-Free Catalytic Boration at the β-Position of α,β-Unsaturated Compounds: A Challenging Asymmetric Induction
    Bonet, Amadeu
    Gulyas, Henrik
    Fernandez, Elena
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (30) : 5130 - 5134
  • [9] Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis
    Burks, Heather E.
    Morken, James P.
    [J]. CHEMICAL COMMUNICATIONS, 2007, (45) : 4717 - 4725
  • [10] Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
    Cao, Jia
    Wang, Guoqiang
    Gao, Liuzhou
    Cheng, Xu
    Li, Shuhua
    [J]. CHEMICAL SCIENCE, 2018, 9 (15) : 3664 - 3671
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