Sustainable Flow Oppenauer Oxidation of Secondary Benzylic Alcohols with a Heterogeneous Zirconia Catalyst

被引：34
作者：
Chorghade, Rajeev [1 ]
Battilocchio, Claudio [1 ]
Hawkins, Joel M. [2 ]
Ley, Steven V. [1 ]
机构：
[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England
[2] Pfizer Worldwide Res & Dev, Groton, CT 06340 USA
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 22期
关键词：
AEROBIC OXIDATION; TRANSFER HYDROGENATION; EFFICIENT; KETONES; ALDEHYDES;
D O I：
10.1021/ol4027107
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A flow chemistry process for the Oppenauer oxidation of benzylic secondary alcohols using partially hydrated zirconium oxide and a simple carbonyl containing oxidant such as acetone, cyclohexanone, and neopentanal is reported. The heterogeneous oxidative system could be applied to a wide range of functionalized alcohol substrates, allowing clean and fast delivery of ketone products within a few minutes between 40 and 100 degrees C.
引用
收藏
页码：5698 / 5701
页数：4
相关论文
共 38 条
  • [1] THE OXIDATION POTENTIALS OF ALDEHYDES AND KETONES
    ADKINS, H
    ELOFSON, RM
    ROSSOW, AG
    ROBINSON, CC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (11) : 3622 - 3629
  • [2] Ruthenium-catalyzed Oppenauer-type oxidation of 3 beta-hydroxy steroids. A highly efficient entry into the steroidal hormones with 4-en-3-one functionality
    Almeida, MLS
    Kocovsky, P
    Backvall, JE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) : 6587 - 6590
  • [3] Oxidation potentials of ketones and an aldehyde
    Baker, RH
    Adkins, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 : 3305 - 3314
  • [4] A Machine-Assisted Flow Synthesis of SR48692: A Probe for the Investigation of Neurotensin Receptor-1
    Battilocchio, Claudio
    Deadman, Benjamin J.
    Nikbin, Nikzad
    Kitching, Matthew O.
    Baxendale, Ian R.
    Ley, Steven V.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (24) : 7917 - 7930
  • [5] A Mild and Efficient Flow Procedure for the Transfer Hydrogenation of Ketones and Aldehydes using Hydrous Zirconia
    Battilocchio, Claudio
    Hawkins, Joel M.
    Ley, Steven V.
    [J]. ORGANIC LETTERS, 2013, 15 (09) : 2278 - 2281
  • [6] Oppenauer's oxidation by paraformaldehyde of piperonyl alcohol to heliotropine
    Borzatta, V.
    Capparella, E.
    Chiappino, R.
    Impala, D.
    Poluzzi, E.
    Vaccari, A.
    [J]. CATALYSIS TODAY, 2009, 140 (1-2) : 112 - 116
  • [7] Iron-Catalyzed Oppenauer-Type Oxidation of Alcohols
    Coleman, Michael G.
    Brown, Alec N.
    Bolton, Brett A.
    Guan, Hairong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) : 967 - 970
  • [8] Towards an Efficient Preparation of Hydromorphone
    Csuk, Rene
    Vasileva, Galina
    Barthel, Alexander
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (18): : 2840 - 2842
  • [9] MEERWEIN-PONNDORF-VERLEY REDUCTIONS AND OPPENAUER OXIDATIONS - AN INTEGRATED APPROACH
    DEGRAAUW, CF
    PETERS, JA
    VANBEKKUM, H
    HUSKENS, J
    [J]. SYNTHESIS-STUTTGART, 1994, (10): : 1007 - 1017
  • [10] A Versatile Ruthenium(II)-NNC Complex Catalyst for Transfer Hydrogenation of Ketones and Oppenauer-Type Oxidation of Alcohols
    Du, Wangming
    Wang, Liandi
    Wu, Ping
    Yu, Zhengkun
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (37) : 11550 - 11554
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