Polymer-mounted N3=P(MeNCH2CH2)3N: a green, efficient and recyclable catalyst for room-temperature transesterifications and amidations of unactivated esters

被引：14

作者：

Chintareddy, Venkat Reddy ^{[1
]}

Ho, Hung-An ^{[1
]}

Sadow, Aaron D. ^{[1
]}

Verkade, John G. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 49期

基金：

美国国家科学基金会;

关键词：

Merrifield resin; Solid-supported catalyst; Reusability; Transesterification; Amidation; Azidoproazaphosphatrane; N-HETEROCYCLIC CARBENES; SOLID-SUPPORTED REAGENTS; HETEROGENEOUS CATALYST; METAL-COMPLEXES; ARYL BROMIDES; ESTERIFICATION; BIODIESEL; AMINATION; CHLORIDES; SECONDARY;

D O I：

10.1016/j.tetlet.2011.09.102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Merrifield resin-supported N-3=P(MeNCH2CH2)(3)N shows excellent activity in the transesterification of higher esters such as glyceryl tribenzoate to methyl esters. The catalyst was successfully cycled 20 times (albeit with an increase in reaction time) without compromising yield up to the 20th cycle. The catalyst also showed good performance in amidation reactions of unactivated esters with amino alcohols. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6523 / 6529

页数：7

共 67 条

[31] N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols [J].

Movassaghi, M ;

Schmidt, MA .

ORGANIC LETTERS, 2005, 7 (12) :2453-2456

[32] N-heterocyclic carbenes: Reagents, not just ligands! [J].

Nair, V ;

Bindu, S ;

Sreekumar, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5130-5135

[33] Expanding the catalytic activity of nucleophilic N-heterocyclic carbenes for transesterification reactions [J].

Nyce, GW ;

Lamboy, JA ;

Connor, EF ;

Waymouth, RM ;

Hedrick, JL .

ORGANIC LETTERS, 2002, 4 (21) :3587-3590

[34] METHODS OF PREPARATION - FATTY ACID ESTERS OF SUCROSE [J].

OSIPOW, L ;

SNELL, FD ;

YORK, WC ;

FINCHLER, A .

INDUSTRIAL AND ENGINEERING CHEMISTRY, 1956, 48 (09) :1459-1462

[35] EMULSION STABILITY [J].

OSIPOW, L ;

BIRSAN, S ;

DEESNELL, F .

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1957, 34 (01) :34-38

[36] Toward ideal (Trans) esterification by use of fluorous distannoxane catalysts [J].

Otera, J .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (05) :288-296

[37] TRANSESTERIFICATION [J].

OTERA, J .

CHEMICAL REVIEWS, 1993, 93 (04) :1449-1470

[38] ETHANOLAMIDES OF SOME MONOCARBOXYLIC AND DICARBOXYLIC ACIDS [J].

PHILLIPS, AP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (12) :5557-5559

[39] Selective catalytic transesterification, transthiolesterification, and protection of carbonyl compounds over natural kaolinitic clay [J].

Ponde, DE ;

Deshpande, VH ;

Bulbule, VJ ;

Sudalai, A ;

Gajare, AS .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1058-1063

[40] A simple and efficient procedure for transesterification catalyzed by indium triiodide [J].

Ranu, BC ;

Dutta, P ;

Sarkar, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :6027-6028

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