Preparation of flavin-containing mesoporous network polymers and their catalysis

被引:4
作者
Arakawa, Yukihiro [1 ]
Sato, Fumiaki [1 ]
Ariki, Kenta [1 ]
Minagawa, Keiji [1 ,2 ]
Imada, Yasushi [1 ]
机构
[1] Tokushima Univ, Dept Appl Chem, Tokushima 7708506, Japan
[2] Tokushima Univ, Inst Liberal Arts & Sci, Tokushima 7708502, Japan
关键词
Flavin; Polymer-supported catalyst; Hydrogenation; Photooxidation; VISIBLE-LIGHT; RIBOFLAVIN TETRAACETATE; AEROBIC PHOTOOXIDATION; ACTIVATION; SULFIDES;
D O I
10.1016/j.tetlet.2020.151710
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Riboflavin tetramethacrylate (RFlTMA) was prepared as a flavin monomer and copolymerized with ethylene glycol dimethacrylate (EGDMA) under polymerization-induced phase separation conditions. The resulting flavin-containing mesoporous network polymer, poly(RFlTMA-co-EGDMA), was found to be a more effective catalyst than riboflavin tetraacetate (RFlTA), a soluble analogue, for aerobic hydrogenation of olefins despite its heterogeneity, which allowed for its multiple recovery and reuse through simple filtrations and washings without loss in catalytic activity. In addition, the polymeric flavin was demonstrated to be utilized also as an effective photocatalyst in the oxidation of benzyl alcohols. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 31 条
[1]   Design of peptide-containing N5-unmodified neutral flavins that catalyze aerobic oxygenations [J].
Arakawa, Yukihiro ;
Yamanomoto, Ken ;
Kita, Hazuki ;
Minagawa, Keiji ;
Tanaka, Masami ;
Haraguchi, Naoki ;
Itsuno, Shinichi ;
Imada, Yasushi .
CHEMICAL SCIENCE, 2017, 8 (08) :5468-5475
[2]   Synthesis of Insoluble Polystyrene-Supported Flavins and Their Catalysis in Aerobic Reduction of Olefins [J].
Arakawa, Yukihiro ;
Kawachi, Risa ;
Tezuka, Yoshihiko ;
Minagawa, Keiji ;
Imada, Yasushi .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2017, 55 (10) :1706-1713
[3]   Efficient Recovery and Reuse of an Immobilized Peptidic Organocatalyst [J].
Arakawa, Yukihiro ;
Wiesner, Markus ;
Wennemers, Helma .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1201-1206
[4]   Artificial Flavin Systems for Chemoselective and Stereoselective Oxidations [J].
Cibulka, Radek .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (05) :915-932
[5]   Photooxidation of Sulfides to Sulfoxides Mediated by Tetra-O-Acetylriboflavin and Visible Light [J].
Dad'ova, Jitka ;
Svobodova, Eva ;
Sikorski, Marek ;
Koenig, Burkhard ;
Cibulka, Radek .
CHEMCATCHEM, 2012, 4 (05) :620-623
[6]   Recent Developments in Flavin-based Catalysis [J].
de Gonzalo, Gonzalo ;
Fraaije, Marco W. .
CHEMCATCHEM, 2013, 5 (02) :403-415
[7]  
DOLLIMORE D, 1964, J APPL CHEM, V14, P109
[8]   LED-Illuminated NMR Studies of Flavin-Catalyzed Photooxidations Reveal Solvent Control of the Electron-Transfer Mechanism [J].
Feldmeier, Christian ;
Bartling, Hanna ;
Magerl, Kathrin ;
Gschwind, Ruth M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) :1347-1351
[9]   Halogenase-Inspired Oxidative Chlorination Using Flavin Photocatalysis [J].
Hering, Thea ;
Muehldorf, Bernd ;
Wolf, Robert ;
Koenig, Burkhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (17) :5342-5345
[10]   Biomimetic flavin-catalysed reactions for organic synthesis [J].
Iida, H. ;
Imada, Y. ;
Murahashi, S-I. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (28) :7599-7613