Synthesis and Application of Palladium Precatalysts that Accommodate Extremely Bulky Di-tert-butylphosphino Biaryl Ligands

被引：113
作者：
Bruno, Nicholas C. [1 ]
Buchwald, Stephen L. [1 ]
机构：
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 11期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
CATALYZED AMIDATION; COUPLING REACTIONS; ARYL; ALLOWS; ARYLATION; HALIDES; ETHERS;
D O I：
10.1021/ol401208t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of palladacyclic precatalysts that incorporate electron-rich di-fert-butylphosphino biaryl ligands is reported. These precatalysts are easily prepared, and their use provides a general means of employing bulky ligands in palladium-catalyzed cross-coupling reactions. The application of these palladium sources to various C-N and C-O bond-forming processes is also described.
引用
收藏
页码：2876 / 2879
页数：4
相关论文
共 16 条
  • [1] The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans
    Anderson, Kevin W.
    Ikawa, Takashi
    Tundel, Rachel E.
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) : 10694 - 10695
  • [2] A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides
    Biscoe, Mark R.
    Fors, Brett P.
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) : 6686 - +
  • [3] Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions
    Bruno, Nicholas C.
    Tudge, Matthew T.
    Buchwald, Stephen L.
    [J]. CHEMICAL SCIENCE, 2013, 4 (03) : 916 - 920
  • [4] Water-mediated catalyst preactivation: An efficient protocol for C-N cross-coupling reactions
    Fors, Brett P.
    Krattiger, Philipp
    Strieter, Eric
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2008, 10 (16) : 3505 - 3508
  • [5] An efficient system for the Pd-catalyzed cross-coupling of amides and aryl chlorides
    Fors, Brett P.
    Dooleweerdt, Karin
    Zeng, Qingle
    Buchwald, Stephen L.
    [J]. TETRAHEDRON, 2009, 65 (33) : 6576 - 6583
  • [6] A New Palladium Precatalyst Allows for the Fast Suzuki-Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids
    Kinzel, Tom
    Zhang, Yong
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) : 14073 - 14075
  • [7] C-O Cross-Coupling of Activated Aryl and Heteroaryl Halides with Aliphatic Alcohols
    Maligres, Peter E.
    Li, Jing
    Krska, Shane W.
    Schreier, John D.
    Raheem, Izzat T.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) : 9071 - 9074
  • [8] Synthesis of Imidazo[4,5-b]pyridines and Imidazo[4,5-b]pyrazines by Palladium Catalyzed Amidation of 2-Chloro-3-amino-heterocycles
    Rosenberg, Adam J.
    Zhao, Jinbo
    Clark, Daniel A.
    [J]. ORGANIC LETTERS, 2012, 14 (07) : 1764 - 1767
  • [9] A New Biarylphosphine Ligand for the Pd-Catalyzed Synthesis of Diaryl Ethers under Mild Conditions
    Salvi, Luca
    Davis, Nicole R.
    Ali, Siraj Z.
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 170 - 173
  • [10] Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates
    Strotman, Neil A.
    Chobanian, Harry R.
    Guo, Yan
    He, Jiafang
    Wilson, Jonathan E.
    [J]. ORGANIC LETTERS, 2010, 12 (16) : 3578 - 3581
12