Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings

被引：3
|
作者：
Bernauer, Josef [1 ]
Wu, Guojiao [1 ]
Jacobi von Wangelin, Axel [1 ]
机构：
[1] Univ Hamburg, Dept Chem, Martin Luther King Pl 6, D-20146 Hamburg, Germany
来源：
RSC ADVANCES | 2019年 / 9卷 / 54期
基金：
欧洲研究理事会;
关键词：
ALKENE HYDROGENATION; GRIGNARD-REAGENTS; COBALT; METAL; TEMPERATURE; SCOPE;
D O I：
10.1039/c9ra07604b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An iron-catalysed allylation of organomagnesium reagents (alkyl, aryl) with simple allyl acetates proceeds under mild conditions (Fe(OAc)(2) or Fe(acac)(2), Et2O, r.t.) to furnish various alkene and styrene derivatives. Mechanistic studies indicate the operation of a homotopic catalyst. The sequential combination of such iron-catalysed allylation with an iron-catalysed hydrogenation results in overall C(sp(3))-C(sp(3))-bond formation that constitutes an attractive alternative to challenging direct cross-coupling protocols with alkyl halides.
引用
收藏
页码：31217 / 31223
页数：7
相关论文
共 50 条
  • [31] New Directing Groups for Metal-Catalyzed Asymmetric Carbon-Carbon Bond-Forming Processes: Stereoconvergent Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Electrophiles
    Wilsily, Ashraf
    Tramutola, Francesco
    Owston, Nathan A.
    Fu, Gregory C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) : 5794 - 5797
  • [32] Effective Alkyl-Alkyl Cross-Coupling with an Iron-Xantphos Catalyst: Mechanistic and Structural Insights
    Gimeno, Magali
    Aguilera, Maria Camila
    Fleischauer, Valerie E.
    Brennessel, William W.
    Neidig, Michael L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (01)
  • [33] PALLADIUM-CATALYZED ALKYL-ALKYL SUZUKI CROSS- COUPLINGS OF PRIMARY ALKYL BROMIDES AT ROOM TEMPERATURE: (13-CHLOROTRIDECYLOXY) TRIETHYLSILANE
    Lou, Sha
    Fu, Gregory C.
    ORGANIC SYNTHESES, 2010, 87 : 299 - +
  • [34] NHC and nucleophile chelation effects on reactive iron(II) species in alkyl-alkyl cross-coupling
    Fleischauer, Valerie E.
    Munoz, Salvador B., III
    Neate, Peter G. N.
    Brennessel, William W.
    Neidig, Michael L.
    CHEMICAL SCIENCE, 2018, 9 (07) : 1878 - 1891
  • [35] The first applications of carbene ligands in cross-couplings of alkyl electrophiles: Sonogashira reactions of unactivated alkyl bromides and iodides
    Eckhardt, M
    Fu, GC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) : 13642 - 13643
  • [36] Erratum: Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides
    Chi Wai Cheung
    Xile Hu
    Nature Communications, 7
  • [37] Homocoupling-free iron-catalysed twofold C-H activation/cross-couplings of aromatics via transient connection of reactants
    Doba, Takahiro
    Matsubara, Tatsuaki
    Ilies, Laurean
    Shang, Rui
    Nakamura, Eiichi
    NATURE CATALYSIS, 2019, 2 (05) : 400 - 406
  • [38] Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents
    Powell, DA
    Maki, T
    Fu, GC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) : 510 - 511
  • [39] Nickel-catalyzed cross-couplings of secondary alkyl nucleophiles with aryl halides
    Joshi-Pangu, Amruta
    Ganesh, Madhu
    Biscoe, Mark
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [40] Suzuki–Miyaura cross-couplings for alkyl boron reagent: recent developments—a review
    Adnan Ahmed
    Irfan Mushtaq
    Sampath Chinnam
    Future Journal of Pharmaceutical Sciences, 9
12345