Nano-silica PAMAM Dendrimer as a Novel Catalyst for Knoevenagel Reactions

被引:8
作者
Hagiwara, Hisahiro [1 ]
Sekifuji, Masayoshi [1 ]
Tsubokawa, Norio [2 ]
Hoshi, Takashi [2 ]
Suzuki, Toshio [2 ]
机构
[1] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan
[2] Niigata Univ, Fac Engn, Niigata 9502181, Japan
关键词
HETEROGENEOUS AMINE CATALYST; BASE CATALYSTS; REUSABLE CATALYST; WATER; CONDENSATION; ALDEHYDES; EFFICIENT; GEL;
D O I
10.1246/cl.2009.926
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A nano-silica dendrimer, poly(amidoamine)-grafted nanosilica (nano-PAMAM), catalyzed the Knoevenagel reaction of aryl and aliphatic aldehydes with various active methylene compounds at room temperature in good yields. The reaction conditions were mild enough that base-sensitive AcO or acid-sensitive THPO groups remained intact in the products. The catalyst was recycled up to 4 times in 78% average yield.
引用
收藏
页码:926 / 927
页数:2
相关论文
共 19 条
[1]  
Anastas P., 1998, GREEN CHEM THEORY PR
[2]   AMINO-GROUPS IMMOBILIZED ON SILICA-GEL - AN EFFICIENT AND REUSABLE HETEROGENEOUS CATALYST FOR THE KNOEVENAGEL CONDENSATION [J].
ANGELETTI, E ;
CANEPA, C ;
MARTINETTI, G ;
VENTURELLO, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :105-107
[3]   Functionalized micelle-templated silicas (MTS) and their use as catalysts for fine chemicals [J].
Brunel, D .
MICROPOROUS AND MESOPOROUS MATERIALS, 1999, 27 (2-3) :329-344
[4]   Supported organic catalysts:: synthesis of (E)-nitrostyrenes from nitroalkanes and aromatic aldehydes over propylamine supported on MCM-41 silica as a reusable catalyst [J].
Demicheli, G ;
Maggi, R ;
Mazzacani, A ;
Righi, P ;
Sartori, G ;
Bigi, F .
TETRAHEDRON LETTERS, 2001, 42 (12) :2401-2403
[5]   PROPERTIES AND REACTIONS OF YLIDENEMALONONITRILES [J].
FREEMAN, F .
CHEMICAL REVIEWS, 1980, 80 (04) :329-350
[6]   Self-aldol condensation of unmodified aldehyde in supercritical carbon dioxide catalyzed by amine grafted on silica [J].
Hagiwara, H ;
Hamaya, J ;
Hoshi, T ;
Yokoyama, C .
TETRAHEDRON LETTERS, 2005, 46 (03) :393-395
[7]   Sustainable transesterification of β-ketoesters catalyzed by amine grafted on silica gel [J].
Hagiwara, H ;
Koseki, A ;
Isobe, K ;
Shimizu, K ;
Hoshi, T ;
Suzuki, T .
SYNLETT, 2004, (12) :2188-2190
[8]   Conjugate addition of unmodified aldehydes: recycle of heterogeneous amine catalyst and ionic liquid [J].
Hagiwara, H ;
Sayuri, T ;
Okabe, T ;
Hoshi, T ;
Suzuki, T ;
Suzuki, H ;
Shimizu, K ;
Kitayama, Y .
GREEN CHEMISTRY, 2002, 4 (05) :461-463
[9]   Heterogeneous amine catalyst grafted on amorphous silica: An effective organocatalyst for microwave-promoted Michael reaction of 1,3-dicarbonyl compounds in water [J].
Hagiwara, Hisahiro ;
Inotsume, Sachiyo ;
Fukushima, Masakazu ;
Hoshi, Takashi ;
Suzuki, Toshio .
CHEMISTRY LETTERS, 2006, 35 (08) :926-927
[10]   Sequential knoevenagel reaction/Mislow-Evans rearrangement catalyzed by heterogeneous amine grafted on silica in water, leading to γ-hydroxy-α,β-unsaturated nitrile [J].
Hagiwara, Hisahiro ;
Isobe, Kohei ;
Numamae, Ayuko ;
Hoshi, Takashi ;
Suzuki, Toshio .
SYNLETT, 2006, (10) :1601-1603