Silaphenylmercuric Triflate Catalyzed Reactions: Synthesis of a Solid-Supported Mercuric Salt Catalyst

被引:34
作者
Yamamoto, Hirofumi [1 ]
Sasaki, Ikuo [1 ]
Hirai, Yuki [1 ]
Namba, Kosuke [1 ]
Imagawa, Hiroshi [1 ]
Nishizawa, Mugio [1 ]
机构
[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Tokushima 7708514, Japan
关键词
alkynes; cyclization; flow reactor; heterocycles; mercury; POLYMER-INCARCERATED PALLADIUM; INORGANIC HYBRID MATERIALS; REUSABLE CATALYST; MESOPOROUS SILICA; HIGHLY EFFICIENT; RECYCLABLE CATALYSTS; ACTIVE CATALYST; TERMINAL ALKYNE; SUZUKI; COMPLEX;
D O I
10.1002/anie.200804641
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Let it flow, let it flow: A procedure to generate the first solid-supported mercuric salt, silaphenylmercuric triflate, is described. Silaphenylmercuric triflate showed remarkable catalytic activity for an indole synthesis, furanoyne cyclization, arylyne cyclization, and tandem carbocyclizations. An efficient flow reaction system for indole synthesis and arylyne cyclization is also described (see figure). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1244 / 1247
页数:4
相关论文
共 58 条
[11]   Mercaptopropyl-modified mesoporous silica: A remarkable support for the preparation of a reusable, heterogeneous palladium catalyst for coupling reactions [J].
Crudden, CM ;
Sateesh, M ;
Lewis, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :10045-10050
[12]  
Fairlamb I. J. S., 2004, ANGEW CHEM, V116, P1066
[13]   Asymmetric cycloisomerization of 1,6-and 1,7-enynes by transition-metal catalysts [J].
Fairlamb, IJS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1048-1052
[14]   Supramolecular immobilization of a perfluoro-tagged Pd-catalyst with dendritic architectures and application in Suzuki reactions [J].
Garcia-Bernabé, A ;
Tzschucke, CC ;
Bannwarth, W ;
Haag, R .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (10) :1389-1394
[15]   Reusable polymer-supported catalyst for the [3+2] Huisgen cycloaddition in automation protocols [J].
Girard, C ;
Önen, E ;
Aufort, M ;
Beauvière, S ;
Samson, E ;
Herscovici, J .
ORGANIC LETTERS, 2006, 8 (08) :1689-1692
[16]   Practical preparation method of polymer-incarcerated (PI) palladium catalysts using Pd(II) salts [J].
Hagio, H ;
Sugiura, M ;
Kobayashi, S .
ORGANIC LETTERS, 2006, 8 (03) :375-378
[17]   Mercuric triflate-catalyzed reaction of propargyl acetates with water leading vinyl ketones [J].
Imagawa, H ;
Asai, Y ;
Takano, H ;
Hamagaki, H ;
Nishizawa, M .
ORGANIC LETTERS, 2006, 8 (03) :447-450
[18]   Biomimetic tandem cyclization catalyzed by Hg(OTf)2 affording polycarbocycles [J].
Imagawa, H ;
Iyenaga, T ;
Nishizawa, M .
SYNLETT, 2005, (04) :703-705
[19]   Mercuric triflate-catalyzed tandem cyclization leading to polycarbocycles [J].
Imagawa, H ;
Iyenaga, T ;
Nishizawa, M .
ORGANIC LETTERS, 2005, 7 (03) :451-453
[20]   Mercuric triflate-catalyzed synthesis of 2-methylfurans from 1-alkyn-5-ones [J].
Imagawa, H ;
Kurisaki, T ;
Nishizawa, M .
ORGANIC LETTERS, 2004, 6 (21) :3679-3681