Synthesis of magnetically recoverable imidazolium hydrogen carbonate and its application as an N-heterocyclic carbene catalyst to cyanosilylation of aldehydes and ketones

被引:13
作者
Fujii, Akira [1 ]
Choi, Jun-Chul [1 ]
Fujita, Ken-ichi [1 ]
机构
[1] Natl Inst Adv Ind Sci & Technol, Tsukuba Cent 5,1-1-1 Higashi, Tsukuba, Ibaraki 3058565, Japan
关键词
Magnetite; Catalysis; Imidazollum hydrogen carbonate; Cyanosilylation; RETRIEVABLE CATALYSTS; OSMIUM CATALYSTS; ORGANOCATALYSTS; DIHYDROXYLATION; CARBOXYLATES; HYDROLYSIS; SUPPORTS; OLEFINS; NHCS; CO;
D O I
10.1016/j.tetlet.2017.03.006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We prepared a magnetically recoverable imidazolium hydrogen carbonate by immobilizing an imidazolium hydrogen carbonate on magnetite and applied it as an N-heterocyclic carbene catalyst to the cyanosilylation of aldehydes and ketones. By employing the magnetite-supported imidazolium hydrogen carbonate as a catalyst, the cyanosilylation proceeded at 60 degrees C to provide the corresponding trimethylsilylated cyanohydrin in a fair chemical yield. Moreover, after the reaction, the magnetic catalyst was readily recovered by use of an external magnet and could be reused up to five times. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1515 / 1518
页数:4
相关论文
共 41 条
[1]   A magnetic nanoparticle catalyzede co-friendly synthesis of cyanohydrins in a deep eutectic solvent [J].
Azizi, Najmedin ;
Rahimi, Zahra ;
Alipour, Masoumeh .
RSC ADVANCES, 2015, 5 (75) :61191-61198
[2]   Magnetically retrievable catalysts for asymmetric synthesis [J].
Baig, R. B. Nasir ;
Nadagouda, Mallikarjuna N. ;
Varma, Rajender S. .
COORDINATION CHEMISTRY REVIEWS, 2015, 287 :137-156
[3]   Magnetically retrievable catalysts for organic synthesis [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
CHEMICAL COMMUNICATIONS, 2013, 49 (08) :752-770
[4]   Poly(ionic liquid)s Based on Imidazolium Hydrogen Carbonate Monomer Units as Recyclable Polymer-Supported N-Heterocyclic Carbenes: Use in Organocatalysis [J].
Coupillaud, Paul ;
Pinaud, Julien ;
Guidolin, Nicolas ;
Vignolle, Joan ;
Fevre, Mareva ;
Veaudecrenne, Ellen ;
Mecerreyes, David ;
Taton, Daniel .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (21) :4530-4540
[5]   Single-component catalyst/initiators for the organocatalytic ring-opening polymerization of lactide [J].
Csihony, S ;
Culkin, DA ;
Sentman, AC ;
Dove, AP ;
Waymouth, RM ;
Hedrick, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9079-9084
[6]   Magnetic nanoparticle supports for asymmetric catalysts [J].
Dalpozzo, Renato .
GREEN CHEMISTRY, 2015, 17 (07) :3671-3686
[7]   Betaine Adducts of N-Heterocyclic Carbenes: Synthesis, Properties, and Reactivity [J].
Delaude, Lionel .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (13) :1681-1699
[8]   Synthesis and reactivity of subvalent compounds Part 11. Oxidation, hydrogenation and hydrolysis of stable diamino carbenes [J].
Denk, MK ;
Rodezno, JM ;
Gupta, S ;
Lough, AJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :242-253
[9]   The Measure of All Rings-N-Heterocyclic Carbenes [J].
Droege, Thomas ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (39) :6940-6952
[10]   Reversible carboxylation of N-heterocyclic carbenes [J].
Duong, HA ;
Tekavec, TN ;
Arif, AM ;
Louie, J .
CHEMICAL COMMUNICATIONS, 2004, (01) :112-113