Facile immobilization of copper(I) acetate on silica: A recyclable and reusable heterogeneous catalyst for azide-alkyne clickable cycloaddition reactions

被引：15

作者：

Aflak, Noura ^{[1
]}

Ben El Ayouchia, Hicham ^{[1
,2
]}

Bahsis, Lahoucine ^{[1
]}

Anane, Hafid ^{[1
]}

Laamari, Rachid ^{[1
]}

Pascual-Alvarez, Alejandro ^{[2
]}

Armentano, Donatella ^{[3
]}

Stiriba, Salah-Eddine ^{[1
]}

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 Arcavacata Di Rende, Cosenza, Italy

来源：

POLYHEDRON | 2019年 / 170卷

关键词：

Copper(I) acetate; Silica gel; Immobilization; Heterogeneous catalysis; Click chemistry; 3+2] cycloaddition; Conceptual DFT; 1,3-DIPOLAR CYCLOADDITION; CHEMISTRY; REACTIVITY; INDEX;

D O I：

10.1016/j.poly.2019.06.030

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The structurally well-defined copper(I) acetate was immobilized on silica gel via electrostatic interactions. The catalytic activity of the immobilized catalyst Cu(l)-SiO2 was examined in the click synthesis of 1,2,3-triazoles in water/ethanol at room temperature. The catalyst showed high catalytic activity and regioselectivity for the Huisgen [3+2] cycloaddition reaction between terminal alkynes and azides. The catalyst was recovered by simple filtration and reused for up to five times. The analysis of the local electrophilicity/nucleophilicity has been performed on the dinuclear copper-acetylide complex intermediate. Conceptual DFT (CDFT) analysis enabled the explanation of the formation of 1,2,3-triazole in a regioselective manner. FT-IR, XRPD, SEM and ICP techniques were used to characterize the immobilized catalyst. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：630 / 638

页数：9

共 42 条

[31]

Parr R.G., 1995, DENSITY FUNCTIONAL T, pi, DOI [10.1093/oso/9780195092769.001.0001, DOI 10.1007/978-94-009-9027-2_2]

[32] Electrophilicity index [J].

Parr, RG ;

Von Szentpály, L ;

Liu, SB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) :1922-1924

[33] ABSOLUTE HARDNESS - COMPANION PARAMETER TO ABSOLUTE ELECTRONEGATIVITY [J].

PARR, RG ;

PEARSON, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7512-7516

[34] Copper-alginates: a blopolymer supported Cu(II) catalyst for 1,3-dipolar cycloaddition of alkynes with azides and oxidative coupling of 2-naphthols and phenols in water [J].

Reddy, K. Rajender ;

Rajgopal, K. ;

Kantam, M. Lakshmi .

CATALYSIS LETTERS, 2007, 114 (1-2) :36-40

[35] Benzimidazole and related Ligands for Cu-catalyzed azide-alkyne cycloaddition [J].

Rodionov, Valentin O. ;

Presolski, Stanislav I. ;

Gardinier, Sean ;

Lim, Yeon-Hee ;

Finn, M. G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12696-12704

[36]

Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO

[37]

2-4

[38] Effect of size of copper nanoparticles on its catalytic behaviour in Ullman reaction [J].

Samim, Mohd. ;

Kaushik, N. K. ;

Maitra, Amarnath .

BULLETIN OF MATERIALS SCIENCE, 2007, 30 (05) :535-540

[39] Ring-Expanded N-Heterocyclic Carbenes for Copper-Mediated Azide-Alkyne Click Cycloaddition Reactions [J].

Sebest, Filip ;

Dunsford, Jay J. ;

Adams, Matthew ;

Pivot, Jeremy ;

Newman, Paul D. ;

Diez-Gonzalez, Silvia .

CHEMCATCHEM, 2018, 10 (09) :2041-2045

[40] Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper-Catalyzed Azide-Alkyne Cycloaddition [J].

Shao, Changwei ;

Cheng, Guolin ;

Su, Deyong ;

Xu, Jimin ;

Wang, Xinyan ;

Hu, Yuefei .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1587-1592

← 1 2 3 4 5 →