From 'Lab & Light on a Chip' to Parallel Microflow Photochemistry

被引:31
作者
Oelgemoeller, Michael [1 ]
Hoffmann, Norbert [2 ]
Shvydkiv, Oksana [3 ]
机构
[1] James Cook Univ, Sch Pharm & Mol Sci, Townsville, Qld 4811, Australia
[2] Univ Reims, CNRS, Inst Chim Mol Reims, UFR Sci, F-51687 Reims 02, France
[3] European Mol Biol Lab EMBL, Genome Biol Unit, D-69117 Heidelberg, Germany
基金
澳大利亚研究理事会;
关键词
ELECTRON-DEFICIENT ALKENES; PHOTOSENSITIZED ADDITION; 2+2 PHOTOCYCLOADDITION; HIGHLY EFFICIENT; GREEN CHEMISTRY; TERTIARY-AMINES; FLOW; ISOPROPANOL; FURANONES; MICROPHOTOCHEMISTRY;
D O I
10.1071/CH13591
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Continuous-flow microreactors offer major advantages for photochemical applications. This mini-review summarizes the technological development of microflow devices in the Applied and Green Photochemistry Group at James Cook University, and its associates, from fixed microchips for microscale synthesis to flexible multicapillary systems for parallel photochemistry. Whereas the enclosed microchip offered high space-time-yields, the open capillary-type reactor showed a greater potential for further modifications. Consequently, a 10-microcapillary reactor was constructed and used successfully for process optimization, reproducibility studies, scale-up, and library synthesis. To demonstrate the superiority of microflow photochemistry over conventional batch processes, the reactors were systematically evaluated using alcohol additions to furanones as model reactions. In all cases, the microreactor systems furnished faster conversions, improved product qualities, and higher yields. UVC-induced [2+2] cycloadditions of furanone with alkenes were exemplarily examined in a capillary reactor, thus proving the broad applicability of this reactor type.
引用
收藏
页码:337 / 342
页数:6
相关论文
共 48 条
  • [1] Photochemical synthesis of a "cage" compound in a microreactor: Rigorous comparison with a batch photoreactor
    Aillet, Tristan
    Loubiere, Karine
    Dechy-Cabaret, Odile
    Prat, Laurent
    [J]. CHEMICAL ENGINEERING AND PROCESSING-PROCESS INTENSIFICATION, 2013, 64 : 38 - 47
  • [2] Microflow photochemistry: UVC-induced [2+2]-photoadditions to furanone in a microcapillary reactor
    Bachollet, Sylvestre
    Terao, Kimitada
    Aida, Shin
    Nishiyama, Yasuhiro
    Kakiuchi, Kiyomi
    Oelgemoeller, Michael
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2015 - 2021
  • [3] The integration of flow reactors into synthetic organic chemistry
    Baxendale, Ian R.
    [J]. JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2013, 88 (04) : 519 - 552
  • [4] Bertrand S, 2000, EUR J ORG CHEM, V2000, P2227
  • [5] Highly efficient photochemical addition of tertiary amines to electron deficient alkenes.: Diastereoselective addition to (5R)-5-Menthyloxy-2[5H]-furanone
    Bertrand, S
    Glapski, C
    Hoffmann, N
    Pete, JP
    [J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3169 - 3172
  • [6] Micro-photochemistry: photochemistry in microstructured reactors. The new photochemistry of the future?
    Coyle, Emma E.
    Oelgemoeller, Michael
    [J]. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2008, 7 (11) : 1313 - 1322
  • [7] Elvira KS, 2013, NAT CHEM, V5, P905, DOI [10.1038/NCHEM.1753, 10.1038/nchem.1753]
  • [8] Continuous-flow synthesis of activated vitamin D3 and its analogues
    Fuse, Shinichiro
    Mifune, Yuto
    Tanabe, Nobutake
    Takahashi, Takashi
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) : 5205 - 5211
  • [9] HIGHLY DIASTEREOSELECTIVE ADDITION OF PHOTOCHEMICALLY GENERATED RADICALS TO (5R)-(-)-MENTHYLOXY-2[5H]-FURANONE - SYNTHESIS OF (-)-TEREBIC ACID
    HOFFMANN, N
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (05) : 879 - 886
  • [10] A practical flow reactor for continuous organic photochemistry
    Hook, BDA
    Dohle, W
    Hirst, PR
    Pickworth, M
    Berry, MB
    Booker-Milburn, KI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (19) : 7558 - 7564