Highly Efficient Continuous Flow Reactions Using Singlet Oxygen as a "Green" Reagent

被引:176
作者
Levesque, Francois
Seeberger, Peter H. [1 ]
机构
[1] Max Planck Inst Colloids & Interfaces, Dept Biomol Syst, D-14476 Potsdam, Germany
关键词
2-PHASE FLOW; GENERATION; GLYCOSYLATION; DEACTIVATION; OPTIMIZATION;
D O I
10.1021/ol2017643
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Described is a new method for the efficient in situ production of singlet oxygen in a simple continuous flow photochemical reactor. The extremely large interfacial area generated by running the biphasic mixture in a narrow channel at a high flow rate ensures high throughput as well as fast and efficient oxidation of various alkenes, 1,3-dienes, and thioethers on a preparative scale.
引用
收藏
页码:5008 / 5011
页数:4
相关论文
共 44 条
[1]   PHOTOOXYGENATION OF OLEFINS IN THE PRESENCE OF TITANIUM(IV) CATALYST - A CONVENIENT ONE-POT SYNTHESIS OF EPOXY ALCOHOLS [J].
ADAM, W ;
BRAUN, M ;
GRIESBECK, A ;
LUCCHINI, V ;
STAAB, E ;
WILL, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) :203-212
[2]   HIV-1 protease inhibitors from inverse design in the substrate envelope exhibit subnanomolar binding to drug-resistant variants [J].
Altman, Michael D. ;
Ali, Akbar ;
Reddy, G. S. Kiran Kumar ;
Nalam, Madhavi N. L. ;
Anjum, Saima Ghafoor ;
Cao, Hong ;
Chellappan, Sripriya ;
Kairys, Visvalclas ;
Fernandes, Miguel X. ;
Gilson, Michael K. ;
Schiffer, Celia A. ;
Rana, Tariq M. ;
Tidor, Bruce .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (19) :6099-6113
[3]   NEW DEVELOPMENTS IN PHOTOCHEMICAL TECHNOLOGY [J].
ANDRE, JC ;
VIRIOT, ML ;
VILLERMAUX, J .
PURE AND APPLIED CHEMISTRY, 1986, 58 (06) :907-916
[4]   SAFETY CONSIDERATIONS IN INDUSTRIAL USE OF ORGANIC PEROXIDES [J].
ARMITAGE, JB ;
STRAUSS, HW .
INDUSTRIAL AND ENGINEERING CHEMISTRY, 1964, 56 (12) :28-&
[5]   Cleaner Continuous Photo-Oxidation Using Singlet Oxygen in Supercritical Carbon Dioxide [J].
Bourne, Richard A. ;
Han, Xue ;
Poliakoff, Martyn ;
George, Michael W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (29) :5322-5325
[6]   Oligosaccharide synthesis in microreactors [J].
Carrel, Frederic R. ;
Geyer, Karolin ;
Codee, Jeroen D. C. ;
Seeberger, Peter H. .
ORGANIC LETTERS, 2007, 9 (12) :2285-2288
[7]   The effect of tube diameter on vertical two-phase flow regimes in small tubes [J].
Chen, L. ;
Tian, Y. S. ;
Karayiannis, T. G. .
INTERNATIONAL JOURNAL OF HEAT AND MASS TRANSFER, 2006, 49 (21-22) :4220-4230
[8]   Micro-photochemistry: photochemistry in microstructured reactors. The new photochemistry of the future? [J].
Coyle, Emma E. ;
Oelgemoeller, Michael .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2008, 7 (11) :1313-1322
[9]   Synthesis and antimalarial activity of trioxaquine derivatives [J].
Dechy-Cabaret, O ;
Benoit-Vical, F ;
Loup, C ;
Robert, A ;
Gornitzka, H ;
Bonhoure, A ;
Vial, H ;
Magnaval, JF ;
Séguéla, JP ;
Meunier, B .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (07) :1625-1636
[10]  
Ehrfeld W., 2000, MICROREACTORS NEW TE, P230