Continuous Reductions and Reductive Aminations Using Solid NaBH4

被引:28
作者
Gilmore, Kerry [1 ]
Vukelic, Stella [2 ]
McQuade, D. Tyler [1 ,3 ]
Koksch, Beate [2 ]
Seeberger, Peter H. [1 ]
机构
[1] Max Planck Inst Colloids & Interfaces, D-14476 Potsdam, Germany
[2] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
[3] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
关键词
FLOW CHEMISTRY; SELECTIVE REDUCTION; CARBONYL-COMPOUNDS; ALDEHYDES; KETONES; CATALYSTS; VERSATILE; TECHNOLOGY; COMPLEXES; EFFICIENT;
D O I
10.1021/op500310s
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Most successful reactions carried out under continuous flow conditions mix homogeneous solutions yielding homogeneous products. Using solids is avoided to prevent pump and reactor clogging; even though solid reagents may often be the best choice for a given transformation. Here we demonstrate that by pumping aldehydes, ketones, or in situ formed imines through a specially formulated NaBH4 column results in efficient reductions. The column design and performance characteristics, along with substrate scope, are discussed.
引用
收藏
页码:1771 / 1776
页数:6
相关论文
共 54 条
  • [1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
    AbdelMagid, AF
    Carson, KG
    Harris, BD
    Maryanoff, CA
    Shah, RD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3849 - 3862
  • [2] Advanced organic synthesis using microreactor technology
    Ahmed-Omer, Batoul
    Brandt, Johan C.
    Wirth, Thomas
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) : 733 - 740
  • [3] High loading polymer reagents based on polycationic Ultraresins. Polymer-supported reductions and oxidations with increased efficiency
    Barth, M
    Shah, STA
    Rademann, J
    [J]. TETRAHEDRON, 2004, 60 (39) : 8703 - 8709
  • [4] Improving solid-supported catalyst productivity by using simplified packed-bed microreactors
    Bogdan, Andrew R.
    Mason, Brian P.
    Sylvester, Kevin T.
    McQuade, D. Tyler
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1698 - 1701
  • [5] Application of Metal-Based Reagents and Catalysts in Microstructured Flow Devices
    Chinnusamy, Tamilselvi
    Yudha, Salprima S.
    Hager, Markus
    Kreitmeier, Peter
    Reiser, Oliver
    [J]. CHEMSUSCHEM, 2012, 5 (02) : 247 - 255
  • [6] Copper(I)/N-Heterocyclic Carbene (NHC)-Catalyzed Addition of Terminal Alkynes to Trifluoromethyl Ketones for Use in Continuous Reactors
    Correia, Camille A.
    McQuade, D. Tyler
    Seeberger, Peter H.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3517 - 3521
  • [7] BORON HYDRIDES .5. METHANOLYSIS OF SODIUM BOROHYDRIDE
    DAVIS, RE
    GOTTBRATH, JA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (06) : 895 - &
  • [8] ASYMMETRIC BORON-CATALYZED REACTIONS
    DELOUX, L
    SREBNIK, M
    [J]. CHEMICAL REVIEWS, 1993, 93 (02) : 763 - 784
  • [9] Flow Synthesis of Substituted γ- Lactones by Consecutive Photocatalytic/Reductive Reactions
    Fagnoni, Maurizio
    Bonassi, Filippo
    Palmieri, Alessandro
    Protti, Stefano
    Ravelli, Davide
    Ballini, Roberto
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) : 753 - 758
  • [10] Facile Stoichiometric Reductions in Flow: An Example of Artemisinin
    Fan, Xiaolei
    Sans, Victor
    Yaseneva, Polina
    Plaza, Dorota D.
    Williams, Jonathan
    Lapkin, Alexei
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (05) : 1039 - 1042