Direct catalytic cross-coupling of alkenyllithium compounds

被引：54
作者：
Hornillos, Valentin [1 ]
Giannerini, Massimo [1 ]
Vila, Carlos [1 ]
Fananas-Mastral, Martin [1 ]
Feringa, Ben L. [1 ]
机构：
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
来源：
CHEMICAL SCIENCE | 2015年 / 6卷 / 02期
基金：
欧洲研究理事会;
关键词：
ORGANOLITHIUM COMPOUNDS; ORTHO-METALATION; ORGANIC HALIDES; CARBON-CARBON; PALLADIUM; ARYL; REAGENTS; STRATEGY; ACETYLATION; VINYLATION;
D O I：
10.1039/c4sc03117b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A catalytic method for the direct cross-coupling of alkenyllithium reagents with aryl and alkenyl halides is described. The use of a catalyst comprising Pd-2(dba)(3)/XPhos allows for the stereoselective preparation of a wide variety of substituted alkenes in high yields under mild conditions. In addition (1-ethoxyvinyl) lithium can be efficiently converted into substituted vinyl ethers which, after hydrolysis, give readily access to the corresponding methyl ketones in a one pot procedure.
引用
收藏
页码：1394 / 1398
页数：5
相关论文
共 70 条
  • [1] General Reaction Conditions for the Palladium-Catalyzed Vinylation of Aryl Chlorides with Potassium Alkenyltrifluoroborates
    Alacid, Emilio
    Najera, Carmen
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) : 8191 - 8195
  • [2] Functions, Therapeutic Applications, and Synthesis of Retinoids and Carotenoids
    Alvarez, Rosana
    Vaz, Belen
    Gronemeyer, Hinrich
    de Lera, Angel R.
    [J]. CHEMICAL REVIEWS, 2014, 114 (01) : 1 - 125
  • [3] Beller M., 2004, TRANSITION METALS FO
  • [4] Board J, 2013, PLATIN MET REV, V57, P234, DOI 10.1595/147106713X672311
  • [5] Recent advances in the use of temporary silicon tethers in metal-mediated reactions
    Bracegirdle, Sonia
    Anderson, Edward A.
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) : 4114 - 4129
  • [6] "The Great Beauty" of organolithium chemistry: a land still worth exploring
    Capriati, Vito
    Perna, Filippo M.
    Salomone, Antonio
    [J]. DALTON TRANSACTIONS, 2014, 43 (38) : 14204 - 14210
  • [7] Selected patented cross-coupling reaction technologies
    Corbet, Jean-Pierre
    Mignani, Gerard
    [J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2651 - 2710
  • [8] de Meijere A., 2004, Metal - Catalysed Cross - coupling Reactions
  • [9] Denmark S. E., 2012, ACCOUNTS CHEM RES, V45, P864
  • [10] Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods
    Denmark, Scott E.
    Regen, Christopher S.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1486 - 1499
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