Ir-catalysed formation of C-F bonds. From allylic alcohols to α-fluoroketones

被引:50
作者
Ahlsten, Nanna [1 ]
Martin-Matute, Belen [1 ]
机构
[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden
基金
瑞典研究理事会;
关键词
CARBONYL-COMPOUNDS; REDOX ISOMERIZATION; EFFICIENT SYNTHESIS; FLUORINATION; KETONES; RHODIUM; ALDOLS; COMPLEXES; ALDEHYDES; INSIGHT;
D O I
10.1039/c1cc12653a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel iridium-catalysed tandem isomerisation/C-F bond formation from allylic alcohols and Selectfluor (R) to prepare alpha-fluorinated ketones as single constitutional isomers is reported.
引用
收藏
页码:8331 / 8333
页数:3
相关论文
共 44 条
  • [1] Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature
    Ahlsten, Nanna
    Lundberg, Helena
    Martin-Matute, Belen
    [J]. GREEN CHEMISTRY, 2010, 12 (09) : 1628 - 1633
  • [2] Rhodium-Catalysed Coupling of Allylic, Homoallylic, and Bishomoallylic Alcohols with Aldehydes and N-Tosylimines: Insights into the Mechanism
    Ahlsten, Nanna
    Martin-Matute, Belen
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) : 2657 - 2666
  • [3] Efficient Synthesis of β-Hydroxy Ketones from Allylic Alcohols by Catalytic Formation of Ruthenium Enolates
    Bartoszewicz, Agnieszka
    Livendahl, Madeleine
    Martin-Matute, Belen
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (34) : 10547 - 10550
  • [4] Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers
    Belanger, Etienne
    Cantin, Katy
    Messe, Olivier
    Tremblay, Melanie
    Paquin, Jean-Francois
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) : 1034 - 1035
  • [5] B(C6F5)3 catalyzed hydrosilation of enones and silyl enol ethers
    Blackwell, JM
    Morrison, DJ
    Piers, WE
    [J]. TETRAHEDRON, 2002, 58 (41) : 8247 - 8254
  • [6] Fluorine in medicinal chemistry
    Böhm, HJ
    Banner, D
    Bendels, S
    Kansy, M
    Kuhn, B
    Müller, K
    Obst-Sander, U
    Stahl, M
    [J]. CHEMBIOCHEM, 2004, 5 (05) : 637 - 643
  • [7] From allylic alcohols to aldols by using iron carbonyls as catalysts:: Computational study on a novel tandem isomerization-aldolization reaction
    Branchadell, V
    Crévisy, C
    Grée, R
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) : 5795 - 5803
  • [8] Bis(allyl)-ruthenium(IV) complexes as highly efficient catalysts for the redox isomerization of allylic alcohols into carbonyl compounds in organic and aqueous media:: Scope, limitations, and theoretical analysis of the mechanism
    Cadierno, V
    García-Garrido, SE
    Gimeno, J
    Varela-Alvarez, A
    Sordo, JA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) : 1360 - 1370
  • [9] Ruthenium-catalyzed isomerizations of allylic and propargylic alcohols in aqueous and organic media: Applications in synthesis
    Cadierno, Victorio
    Crochet, Pascale
    Gimeno, Jose
    [J]. SYNLETT, 2008, (08) : 1105 - 1124
  • [10] Fluorine & chirality: how to create a nonracemic stereogenic carbon-fluorine centre?
    Cahard, Dominique
    Xu, Xiuhua
    Couve-Bonnaire, Samuel
    Pannecoucke, Xavier
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) : 558 - 568