Knoevenagel reaction in water catalyzed by amine supported on silica gel

被引:57
作者
Isobe, Kohei [1 ,3 ]
Hoshi, Takashi [2 ]
Suzuki, Toshio [2 ]
Hagiwara, Hisahiro [1 ]
机构
[1] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan
[2] Niigata Univ, Fac Engn, Niigata 9502181, Japan
[3] Ind Res Inst Niigata Prefecture, Niigata 9500915, Japan
关键词
amine catalyst; aqueous reaction; green chemistry; immobilized catalyst; Knoevenagel reaction; recycle; silica gel support;
D O I
10.1007/s11030-005-8107-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
An environmentally benign and sustainable Knoevenagel reaction of aldehyde with ethyl cyanoacetate has been achieved at ambient temperature in water employing 3-aminopropylated silica gel (NAP) as a catalyst. Wide applicability of the reaction is illustrated by the results that not only arylaldehydes of both electronic characters but also aliphatic aldehydes afforded the products. The reaction condition was so mild that aldehydes having acid- or base-sensitive substituents provided substituted alpha-cyano-alpha, beta-unsaturated esters. The catalyst has been efficiently recycled more than five times without any pre-treatment. Catalyst loading was successfully reduced to 0.0029 mmol% (TON = up to 9,226). This protocol was also applicable to the Knoevenagel reaction of malononitrile in good yields in water.
引用
收藏
页码:317 / 320
页数:4
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