Mild and efficient rhodium-catalyzed deoxygenation of ketones to alkanes

被引:15
|
作者
Argouarch, Gilles [1 ]
机构
[1] Univ Rennes, CNRS, UMR 6226, ISCR, F-35000 Rennes, France
关键词
AZIDE-ALKYNE CYCLOADDITION; REDUCTIVE DEOXYGENATION; AROMATIC KETONES; ARYL KETONES; ALDEHYDES; HYDROGENOLYSIS; HYDROGENATION; ALCOHOLYSIS; ENONES;
D O I
10.1039/c9nj02954k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new and simple method for the deoxygenation of ketones to alkanes is presented. Most substrates are reduced under mild conditions by triethylsilane in the presence of catalytic amounts of [Rh(mu-Cl)(CO)(2)](2). This system selectively provides the methylene hydrocarbons in good to excellent yields starting from acetophenones and diaryl ketones. A rapid examination of the reaction pathway suggests that the ketone is first converted into an alcohol, which then undergoes hydrogenolysis to give the alkane.
引用
收藏
页码:11041 / 11044
页数:4
相关论文
共 50 条
  • [41] Rhodium-Catalyzed Branched and Enantioselective Direct α-Allylic Alkylation of Simple Ketones with Alkynes
    Xie, Liyu
    Yang, Haijian
    Ma, Mingliang
    Xing, Dong
    ORGANIC LETTERS, 2020, 22 (05) : 2007 - 2011
  • [42] Rhodium-catalyzed 1,4-addition of terminal alkynes to vinyl ketones
    Lerum, RV
    Chisholm, JD
    TETRAHEDRON LETTERS, 2004, 45 (35) : 6591 - 6594
  • [43] Rhodium-catalyzed asymmetric transfer hydrogenation of alkyl and aryl ketones in aqueous media
    Ahlford, Katrin
    Lind, Jesper
    Maler, Lena
    Adolfsson, Hans
    GREEN CHEMISTRY, 2008, 10 (08) : 832 - 835
  • [44] Unexpected chemoselectivity in the rhodium-catalyzed transfer hydrogenation of α,β-unsaturated ketones in ionic liquids
    Baan, Zoltan
    Finta, Zoltan
    Keglevich, Gyoergy
    Hermecz, Istvan
    GREEN CHEMISTRY, 2009, 11 (12) : 1937 - 1940
  • [45] Rate enhancement with a bowl-shaped phosphane in the rhodium-catalyzed hydrosilylation of ketones
    Niyomura, O
    Tokunaga, M
    Obora, Y
    Iwasawa, T
    Tsuji, Y
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (11) : 1287 - 1289
  • [46] Rhodium-catalyzed formylation of organomercurials: Application to efficient polyol synthesis
    Sarraf, ST
    Leighton, JL
    ORGANIC LETTERS, 2000, 2 (20) : 3205 - 3208
  • [47] Rhodium-catalyzed, carbon-carbon bond-activation of unstrained ketones
    Zeng, Rong
    Dong, Guangbin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [48] Efficient Rhodium-Catalyzed Multicomponent Reaction for the Synthesis of Novel Propargylamines
    Rubio-Perez, Laura
    Iglesias, Manuel
    Munarriz, Julen
    Polo, Victor
    Perez-Torrente, Jesus J.
    Oro, Luis A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (49) : 17701 - 17707
  • [49] Phospholes as efficient ancillaries for the rhodium-catalyzed hydroformylation and hydroaminomethylation of estragole
    Oliveira, Kelley C. B.
    Carvalho, Sabrina N.
    Duarte, Matheus F.
    Gusevskaya, Elena V.
    dos Santos, Eduardo N.
    El Karroumi, Jamal
    Gouygou, Maryse
    Urrutigoity, Martine
    APPLIED CATALYSIS A-GENERAL, 2015, 497 : 10 - 16
  • [50] Diphosphonites as highly efficient ligands for enantioselective rhodium-catalyzed hydrogenation
    Reetz, MT
    Gosberg, A
    Goddard, R
    Kyung, SH
    CHEMICAL COMMUNICATIONS, 1998, (19) : 2077 - 2078