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 50 条
  • [1] Synthesis and characterization of boron-substituted carbons
    Shirasaki, T
    Derré, A
    Ménétrier, M
    Tressaud, A
    Flandrois, S
    CARBON, 2000, 38 (10) : 1461 - 1467
  • [2] Enantioselective Synthesis of Boron-Substituted Quaternary Carbons by NHC-Cu-Catalyzed Boronate Conjugate Additions to Unsaturated Carboxylic Esters, Ketones, or Thioesters
    O'Brien, Jeannette M.
    Lee, Kang-sang
    Hoveyda, Amir H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) : 10630 - 10633
  • [3] DISPLACEMENT REACTIONS OF DIBUTYL IODOMETHANEBORONATE AND SYNTHESIS OF BORON-SUBSTITUTED PYRIMIDINES
    MATTESON, DS
    CHENG, TC
    JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (08): : 3055 - &
  • [4] Nickel-catalyzed synthesis of substituted guanidines.
    Bhat, L
    Georg, GI
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U104 - U104
  • [5] Modular Access to Chiral 1,3-Substituted Fragments via Nickel-Catalyzed Arylboration Reaction
    Bao, Yang
    Yao, Tong
    Kong, Weiyu
    Li, Yangyang
    Fu, Ying
    Wu, Dong
    Yin, Guoyin
    CHINESE JOURNAL OF CHEMISTRY, 2025, 43 (03) : 261 - 267
  • [6] Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions
    Desrosiers, Jean-Nicolas
    Hie, Liana
    Biswas, Soumik
    Zatolochnaya, Olga V.
    Rodriguez, Sonia
    Lee, Heewon
    Grinberg, Nelu
    Haddad, Nizar
    Yee, Nathan K.
    Garg, Neil K.
    Senanayake, Chris H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) : 11921 - 11924
  • [7] NICKEL-CATALYZED SYNTHESIS OF CYCLOOCTATETRAENES FROM SUBSTITUTED DIPROPARGYLAMINES
    CHIUSOLI, GP
    PALLINI, L
    TERENGHI, MG
    TRANSITION METAL CHEMISTRY, 1985, 10 (09) : 350 - 351
  • [8] Tale of two isomers: Nickel-catalyzed regiodivergent epoxide ring opening reactions with organic halides
    Zhao, Yang
    Weix, Daniel John
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [9] Synthesis of Acylsilanes via Nickel-Catalyzed Reactions of α-Hydroxyallylsilanes
    Reddy, Gangireddy PavanKumar
    Reddy, J. Satyanarayana
    Das, Saibal
    Roisnel, Thierry
    Yadav, Jhillu S.
    Chandrasekhar, Srivari
    Gree, Rene
    ORGANIC LETTERS, 2013, 15 (07) : 1524 - 1527
  • [10] A multicomponent approach to substituted benzenes involving sequential nickel-catalyzed reactions
    ElDouhaibi, Ahmad Samih
    Lozanov, Mario
    Montgomery, John
    TETRAHEDRON, 2006, 62 (49) : 11460 - 11469