Heterogeneous organic base-catalyzed reactions enhanced by acid supports

被引：125

作者：

Motokura, Ken ^{[1
]}

Tada, Mizuki ^{[1
]}

Iwasawa, Yasuhiro ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 31期

关键词：

D O I：

10.1021/ja0704333

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Amorphous silica-alumina-supported amines (SA-NR2) were found to be excellent heterogeneous catalysts for a variety of carbon-carbon bond-forming reactions, such as cyano-O-ethoxycarbonylation, Michael reaction, and nitro-aldol reaction. These reactions were hard to proceed either with amines alone or on the SA alone. Solid-state C-13 MAS NMR analysis revealed the acid-base interaction of the H+ site and amine group on the SA-NR2 surface, which makes an acid-base dual activation mechanism possible for carbon-carbon bond-forming reactions.

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页码：9540 / +

页数：3

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共 22 条

[11] Towards perfect catalytic asymmetric synthesis: Dual activation of the electrophile and the nucleophile [J].

Ma, JA ;

Cahard, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (35) :4566-4583

[12] Understanding the influence of the immobilization procedure on the catalytic activity of aminopropylsilicas in C-C forming reactions [J].

Macquarrie, DJ ;

Maggi, R ;

Mazzacani, A ;

Sartori, G ;

Sartorio, R .

APPLIED CATALYSIS A-GENERAL, 2003, 246 (01) :183-188

[13] Supported phenolates as efficient catalysts of the Michael reaction. [J].

Macquarrie, DJ .

TETRAHEDRON LETTERS, 1998, 39 (23) :4125-4128

[14] An acidic layered clay is combined with a basic layered clay for one-pot sequential reactions [J].

Motokura, K ;

Fujita, N ;

Mori, K ;

Mizugaki, T ;

Ebitani, K ;

Kaneda, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) :9674-9675

[15] Michael additions of carbonucleophiles to butenone catalyzed by the non-hydride [Ru(O2CH)(CO)2(PPh3)]2 complex [J].

Picquet, M ;

Bruneau, C ;

Dixneuf, PH .

TETRAHEDRON, 1999, 55 (13) :3937-3948

[16] Cationic [2,6-bis(2′-oxazolinyl)phenyl]palladium(II) complexes:: Catalysts for the asymmetric Michael reaction [J].

Stark, MA ;

Jones, G ;

Richards, CJ .

ORGANOMETALLICS, 2000, 19 (07) :1282-1291

[17] Sequential one-pot reactions using the concept of "Site isolation" [J].

Voit, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4238-4240

[18] Direct synthesis and catalytic applications of ordered large pore aminopropyl-functionalized SBA-15 mesoporous materials [J].

Wang, XG ;

Lin, KSK ;

Chan, JCC ;

Cheng, SF .

JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (05) :1763-1769

[19] Catalytic asymmetric cyano-ethoxycarbonylation reaction of aldehydes using a YLi3Tris(binaphthoxide) (YLB) complex:: Mechanism and roles of achiral additives [J].

Yamagiwa, N ;

Tian, J ;

Matsunaga, S ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3413-3422

[20] Amino-functionalized mesoporous silica synthesized by an anionic surfactant templating route [J].

Yokoi, T ;

Yoshitake, H ;

Yamada, T ;

Kubota, Y ;

Tatsumi, T .

JOURNAL OF MATERIALS CHEMISTRY, 2006, 16 (12) :1125-1135