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 50 条

[21] P(MeNCH2CH2)3N:: A highly selective reagent for synthesizing trans-epoxides from aryl aldehydes
Liu, XD
Verkade, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15): : 4560 - 4564
[22] STEPWISE TRANSANNULAR BOND FORMATION BETWEEN BRIDGEHEAD ATOMS IN ZP(MENCH2CH2)3N SYSTEMS
TANG, JS
LARAMAY, MAH
YOUNG, V
RINGROSE, S
JACOBSON, RA
VERKADE, JG
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 241 - ORGN
[23] SYNTHESIS AND REACTIVITY PATTERNS OF NEW PROAZAPHOSPHATRANES AND QUASI-AZAPHOSPHATRANES ZP(MENCH2CH2)3N
TANG, JS
VERKADE, JG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (05) : 1660 - 1664
[24] STEPWISE TRANSANNULAR BOND FORMATION BETWEEN THE BRIDGEHEAD ATOMS IN ZP(MENCH2CH2)3N SYSTEMS
TANG, JS
LARAMAY, MAH
YOUNG, V
RINGROSE, S
JACOBSON, RA
VERKADE, JG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) : 3129 - 3131
[25] CHEMICAL AND STRUCTURAL IMPLICATIONS OF BOND FORMATION BETWEEN THE BRIDGEHEAD ATOMS IN Z-P(MENCH2CH2)3N SYSTEMS
TANG, JS
LARAMAY, MAH
VERKADE, JG
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 75 (1-4): : 205 - 208
[26] P(RNCH2CH2)3N: An efficient room-temperature promoter for the synthesis of a,b-unsaturated esters, fluorides and nitriles using Wadsworth-Emmons phosphonates
Reddy, Venkat Reddy Chinta
Verkade, John G.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
[27] P(RNCH2CH2)3N:: A versatile and efficient catalyst for the conversion of aldoximes to nitriles
Fei, XS
Verkade, JG
[J]. HETEROATOM CHEMISTRY, 1999, 10 (07) : 541 - 543
[28] P(MeNCH2CH2CH2)3N:: An efficient promoter for the generation of nonstable and somewhat stable sulfur ylides from sulfonium salts
Fei, XS
Verkade, JG
[J]. HETEROATOM CHEMISTRY, 1999, 10 (07) : 538 - 540
[29] P(i-PrNCH2CH2)3N: Efficient Catalyst for Synthesizing β-Hydroxyesters and α,β-Unsaturated Esters using α-Trimethylsilylethylacetate (TMSEA)
Wadhwa, Kuldeep
Verkade, John G.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11): : 4368 - 4371
[30] P(RNCH2CH2)3N:: an efficient promoter for the direct synthesis of E-α,β-unsaturated esters
Kisanga, P
D'Sa, B
Verkade, J
[J]. TETRAHEDRON, 2001, 57 (38) : 8047 - 8052

← 1 2 3 4 5 →