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
  • [1] Lithium triisopropyl borates as nucleophiles for Suzuki-Miyaura cross coupling reactions
    Oberli, Matthias A.
    Buchwald, Stephen L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [2] A General Method for Suzuki-Miyaura Coupling Reactions Using Lithium Triisopropyl Borates (vol 14, pg 4606, 2012)
    Oberli, Matthias A.
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2013, 15 (11) : 2892 - 2892
  • [3] Suzuki-Miyaura Coupling Reactions of Fluorohalobenzenes
    Iqbal, Shoaib
    Sharif, Muhammad
    Langer, Peter
    SYNLETT, 2021, 32 (18) : 1784 - 1795
  • [4] Suzuki-Miyaura Coupling Reactions Using Phosphite Ligands
    Jang, Mihee
    Jo, Youngshin
    Oh, Il-Kwon
    Jung, Hyun Min
    Lee, Sunwoo
    SYNTHESIS-STUTTGART, 2009, (12): : 2073 - 2075
  • [5] An Efficient Method for Sterically Demanding Suzuki-Miyaura Coupling Reactions
    Zhao, Qing
    Li, Chengxi
    Senanayake, Chris H.
    Tang, Wenjun
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (07) : 2261 - 2265
  • [6] Synthesis of formylphenylpyridinecarboxylic acids using Suzuki-Miyaura coupling reactions
    Meier, P
    Legraverant, S
    Müller, S
    Schaub, J
    SYNTHESIS-STUTTGART, 2003, (04): : 551 - 554
  • [7] Efficient Suzuki-Miyaura coupling reactions between lithium alkynyltrimethylborates and aryl chlorides
    Torres, GH
    Choppin, S
    Colobert, F
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) : 1450 - 1454
  • [8] Suzuki-Miyaura cross coupling reactions with Phenoldiazonium salts
    Schmidt, Bernd
    Hoelter, Frank
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (13) : 4914 - 4920
  • [9] A General and Special Catalyst for Suzuki-Miyaura Coupling Processes
    Tang, Wenjun
    Capacci, Andrew G.
    Wei, Xudong
    Li, Wenjie
    White, Andre
    Patel, Nitinchandra D.
    Savoie, Jolaine
    Gao, Joe J.
    Rodriguez, Sonia
    Qu, Bo
    Haddad, Nizar
    Lu, Bruce Z.
    Krishnamurthy, Dhileepkumar
    Yee, Nathan K.
    Senanayake, Chris H.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (34) : 5879 - 5883
  • [10] A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles
    Billingsley, Kelvin L.
    Buchwald, Stephen L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) : 4695 - 4698