A General Method for Suzuki-Miyaura Coupling Reactions Using Lithium Triisopropyl Borates

被引:59
|
作者
Oberli, Matthias A. [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
ELECTROPHILIC DISPLACEMENT REACTIONS; BORONIC ACIDS; EFFICIENT SYNTHESIS; ARYL HALIDES; COMPLEXES; PROTODEBORONATION; CATALYST;
D O I
10.1021/ol302063g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Conditions for the Suzuki-Miyaura coupling of lithium triisopropyl borates are reported, as well as a procedure for a one-pot lithiation, borylation, and subsequent Suzuki-Miyaura coupling of various heterocycles with aryl halides. These borate species are much more stable toward protodeboronation than the corresponding boronic acids and can conveniently be stored on benchtop at room temperature.
引用
收藏
页码:4606 / 4609
页数:4
相关论文
共 50 条
  • [41] Versatile Suzuki-Miyaura coupling reaction using diphenylvinylphosphine ligands
    Suzuki, Ken
    Fontaine, Arnaud
    Hori, Yoji
    Kobayashi, Tohru
    SYNLETT, 2007, (20) : 3206 - 3208
  • [42] Suzuki-Miyaura coupling reactions using novel metal oxide supported ionic palladium catalysts
    Lichtenegger, G. J.
    Maier, M.
    Hackl, M.
    Khinast, J. G.
    Goessler, W.
    Griesser, T.
    Kumar, V. S. Phani
    Gruber-Woelfler, H.
    Deshpande, P. A.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2017, 426 : 39 - 51
  • [43] Desulfonative Suzuki-Miyaura Coupling of Sulfonyl Fluorides
    Chatelain, Paul
    Muller, Cyprien
    Sau, Abhijit
    Brykczynska, Daria
    Bahadori, Maryam
    Rowley, Christopher N.
    Moran, Joseph
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (48) : 25307 - 25312
  • [44] Efficient synthesis of neurotrophic honokiol using Suzuki-Miyaura reactions
    Harada, Kenichi
    Arioka, Chiharu
    Miyakita, Akina
    Kubo, Miwa
    Fukuyama, Yoshiyasu
    TETRAHEDRON LETTERS, 2014, 55 (43) : 6001 - 6003
  • [45] Synthesis of new cellulose ethers using Suzuki-Miyaura reactions
    Goncalves, Cedric
    Favre, Camille
    Feuardant, Pierre
    Klein, Sarah
    Vaca-Garcia, Carlos
    Cecutti, Christine
    Thiebaud-Roux, Sophie
    Vedrenne, Emeline
    CARBOHYDRATE POLYMERS, 2015, 116 : 51 - 59
  • [46] Boron reagent activation in Suzuki-Miyaura coupling
    School of Chemistry, West Mains Road, Edinburgh
    EH9 3JJ, United Kingdom
    RSC Catal. Ser., 21 (322-354): : 322 - 354
  • [47] Suzuki-Miyaura Cross-Coupling of Sulfoxides
    Chen, Qianwei
    Wu, Shufeng
    Yan, Shuqin
    Li, Chengxi
    Abduhulam, Hayrul
    Shi, Yanhui
    Dang, Yanfeng
    Cao, Changsheng
    ACS CATALYSIS, 2020, 10 (15) : 8168 - 8176
  • [48] Suzuki-Miyaura coupling on heterogeneous palladium catalysts
    Papp, A
    Tóth, D
    Molnár, A
    REACTION KINETICS AND CATALYSIS LETTERS, 2006, 87 (02): : 335 - 342
  • [49] Selection of boron reagents for Suzuki-Miyaura coupling
    Lennox, Alastair J. J.
    Lloyd-Jones, Guy C.
    CHEMICAL SOCIETY REVIEWS, 2014, 43 (01) : 412 - 443
  • [50] Transmetalation in the Suzuki-Miyaura Coupling: The Fork in the Trail
    Lennox, Alastair J. J.
    Lloyd-Jones, Guy C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) : 7362 - 7370