A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study

被引：48

作者：

Bahsis, Lahoucine ^{[1
]}

Ben El Ayouchia, Hicham ^{[1
]}

Anane, Hafid ^{[1
]}

Pascual-Alvarez, Alejandro ^{[2
]}

De Munno, Giovanni ^{[3
]}

Julve, Miguel ^{[2
]}

Stiriba, Salah-Eddine ^{[1
,2
]}

机构：

[1] Univ Cadi Ayyad, Fac Polydisciplinaire Safi, LCAM, Safi, Morocco

[2] Univ Valencia, Inst Ciencia Mol ICMol, C Catedrat Jose Beltran 2, Valencia 46980, Spain

[3] Univ Calabria, Dipartimento Chim & Tecnol Chim, I-87036 Cosenza, Italy

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2019年 / 33卷 / 04期

关键词：

aminomethyl polystyrene; click chemistry; CuAAC reaction; DFT methods; heterogeneous catalysis; AZIDE-ALKYNE CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITIONS; HETEROGENEOUS CATALYSTS; HUISGEN CYCLOADDITION; REACTION-MECHANISM; POLYSTYRENE RESIN; TERMINAL ALKYNES; HIGHLY EFFICIENT; SOLID-PHASE; CHEMISTRY;

D O I：

10.1002/aoc.4669

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

In the search for establishing a clickable copper-catalysed (3 + 2) Huisgen azide-alkyne cycloaddition (CuAAC) reaction under strict conditions, in particular in terms of preventing the presence of copper particles/traces in reaction products and using an environmentally benign medium such as water, we describe here the synthesis of an aminomethyl polystyrene-supported copper(I) catalyst (Cu(I)-AMPS) and its characterization by means of Fourier transform infrared and energy-dispersive X-ray spectroscopies and scanning electron microscopy. Cu(I)-AMPS was found to be highly active in the CuAAC reaction of various organic azides with alkynes affording the corresponding 1,4-disubstituted 1,2,3-triazoles in a regioselective manner in air at room temperature and using water as solvent. The insolubility and/or partial solubility of the organic azide and alkyne precursors as well as the heterogeneous Cu(I)-AMPS catalytic system points to the occurrence of the cycloaddition at the organic-water interface 'on water' affording quantitative yields of waterinsoluble 1,2,3-triazoles. A mechanistic study was performed using density functional theory aiming at explaining the observed reactivity and selectivity of the Cu (I)-AMPS catalyst in CuAAC reactions.

引用

页数：15

共 78 条

[71] Direct Evidence of a Dinuclear Copper Intermediate in Cu(I)-Catalyzed Azide-Alkyne Cycloadditions [J].