Nickel-Catalyzed Arylboration of Alkenylarenes: Synthesis of Boron-Substituted Quaternary Carbons and Regiodivergent Reactions

被引:53
作者
Chen, Liang-An [1 ]
Lear, Alan R. [1 ]
Gao, Pin [2 ]
Brown, M. Kevin [1 ]
机构
[1] Indiana Univ, Dept Chem, 800 E Kirkwood Ave, Bloomington, IN 47405 USA
[2] Xi An Jiao Tong Univ, MOE Key Lab Nonequilibrium Synth & Modulat Conden, Xian Key Lab Sustainable Energy Mat Chem, Dept Chem,Sch Sci, Xian 710049, Shaanxi, Peoples R China
基金
美国国家卫生研究院;
关键词
alkenes; arylboration; boron; cross coupling; nickel; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE BORATION; REGIOSELECTIVE ARYLBORATION; ASYMMETRIC-SYNTHESIS; TERTIARY; ESTERS; CARBOBORATION; ALKENES; HYDROBORATION; BORYLATION;
D O I
10.1002/anie.201904861
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method for the construction of boron-substituted quaternary carbons or diarylquaternary carbons by arylboration of highly substituted alkenylarenes is presented. A wide range of alkenes and arylbromides can participate in this reaction thus allowing for a diverse assortment of products to be prepared. In addition, a solvent dependent regiodivergent arylboration of 1,2-disubstituted alkenylarenes is presented, thus greatly increasing the scope of products that can be accessed.
引用
收藏
页码:10956 / 10960
页数:5
相关论文
共 57 条
  • [1] [Anonymous], 2015, Angew. Chem, DOI [10.1002/ange.201500396, DOI 10.1002/ANGE.201500396]
  • [2] [Anonymous], 2016, ANGEW CHEM
  • [3] [Anonymous], 2016, ANGEW CHEM
  • [4] [Anonymous], 2021, J SCI FOOD AGR, DOI DOI 10.1002/JSFA.11414
  • [5] Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides
    Atack, Thomas C.
    Cook, Silas P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (19) : 6139 - 6142
  • [6] Bergmann, 2019, ANGEW CHEM, V131, P1733
  • [7] Catalyst-Controlled 1,2-and 1,1-Arylboration of -Alkyl Alkenyl Arenes
    Bergmann, Allison M.
    Dorn, Stanna K.
    Smith, Kevin B.
    Logan, Kaitlyn M.
    Brown, M. Kevin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) : 1719 - 1723
  • [8] Hydroxyl-Directed Stereoselective Diboration of Alkenes
    Blaisdell, Thomas P.
    Caya, Thomas C.
    Zhang, Liang
    Sanz-Marco, Amparo
    Morken, James P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (26) : 9264 - 9267
  • [9] An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes
    Buslov, Ivan
    Song, Fang
    Hu, Xile
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) : 12295 - 12299
  • [10] Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes
    Chakrabarty, Suman
    Takacs, James M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (17) : 6066 - 6069