Palladium-Catalyzed Heck-Type Cross-Couplings of Unactivated Alkyl Iodides

被引：133
|
作者：
McMahon, Caitlin M. [1 ]
Alexanian, Erik J. [1 ]
机构：
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 23期
关键词：
alkenes; alkyl halides; cross-coupling; homogeneous catalysis; palladium; FREE-RADICALS; DERIVATIVES; ALKENYLATION; GENERATION; COMPLEXES; SECONDARY; BROMIDES; ALKENES; HALIDES; SYSTEM;
D O I：
10.1002/anie.201311323
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium-catalyzed, intermolecular Heck-type coupling of alkyl iodides and alkenes is described. This process is successful with a variety of primary and secondary unactivated alkyl iodides as reaction partners, including those with hydrogen atoms in the beta position. The mild catalytic conditions enable intermolecular C-C bond formations with a diverse set of alkyl iodides and alkenes, including substrates containing base- or nucleophile-sensitive functionality.
引用
收藏
页码：5974 / 5977
页数：4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    McMahen, Rebecca L.
    Alexanian, Erik J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) : 20146 - 20148
  • [2] Palladium-Catalyzed Carbonylative Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    Alexanian, Erik J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12823 - 12825
  • [3] Palladium-catalyzed intermolecular Heck-type reactions with alkyl iodides
    McMahon, Caitlin
    Alexanian, Erik
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [4] Suzuki cross-couplings of unactivated secondary alkyl bromides and iodides
    Zhou, J
    Fu, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) : 1340 - 1341
  • [5] Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides
    Fan, Tao
    Meng, Wei-Dong
    Zhang, Xingang
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 2610 - 2616
  • [6] Palladium-Catalyzed Desulfinative Cross-Couplings
    Gombert, Antoine de
    Willis, Michael C.
    [J]. TRENDS IN CHEMISTRY, 2020, 2 (09): : 865 - 866
  • [7] Palladium-catalyzed cross-couplings of allylic phosphates
    Maslak, Veselin
    Tokic-Vujosevic, Zorana
    Saicic, Radomir N.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (16) : 1858 - 1860
  • [8] Palladium-catalyzed micellar cross-couplings: An outlook
    Ansari, Tharique N.
    Gallou, Fabrice
    Handa, Sachin
    [J]. COORDINATION CHEMISTRY REVIEWS, 2023, 488
  • [9] Development of palladium-catalyzed migrative cross-couplings
    Baudoin, Olivier
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [10] Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
    Teng, Shenghan
    Tessensohn, Malcolm E.
    Webster, Richard D.
    Zhou, Jianrong Steve
    [J]. ACS CATALYSIS, 2018, 8 (08): : 7439 - 7444
12345