REUSABLE POLYMER-SUPPORTED 2,2′-BIARYLPYRIDINE-COPPER COMPLEXES FOR HUISGEN [3+2] CYCLOADDITION IN WATER

被引：11

作者：

Suzuka, Toshimasa ^{[1
]}

Kawahara, Yamato ^{[1
]}

Ooshiro, Kazumasa ^{[1
]}

Nagamine, Takuya ^{[1
]}

Ogihara, Kazuhito ^{[1
]}

Higa, Matsutake ^{[1
]}

机构：

[1] Univ Ryukyus, Dept Chem Biol & Marine Sci, Okinawa 9030213, Japan

来源：

HETEROCYCLES | 2012年 / 85卷 / 03期

关键词：

Copper; Terpyridine; Click Chemistry; Triazole; Azide; CLICK CHEMISTRY; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; 1,3-DIPOLAR CYCLOADDITION; CATALYZED CYCLOADDITION; EFFICIENT SYNTHESIS; ORGANIC AZIDES; LIGAND-FREE; ALKYNES; COPPER(I); ANALOGS;

D O I：

10.3987/COM-11-12405

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polymer-supported 2,2'-biarylpyridine copper complexes were prepared and found to promote the Huisgen [3+2] cycloaddition reaction between azides and alkynes in water to give the corresponding triazoles in up to 95% isolated yield. The catalyst was recovered and reused several times without any loss in catalytic activity. ICP-AES analysis of the aqueous phase revealed barely detectable levels of copper residue.

引用

页码：615 / 626

页数：12

共 50 条

[41] Copper-Catalyzed Huisgen [3+2] Cycloaddition of Gold(I) Alkynyls with Benzyl Azide. Syntheses, Structures, and Optical Properties
Partyka, David V.
Gao, Lei
Teets, Thomas S.
Updegraff, James B., III
Deligonul, Nihal
Gray, Thomas G.
ORGANOMETALLICS, 2009, 28 (21) : 6171 - 6182
[42] Organocatalysis "on water''.: Regioselective [3+2]-cycloaddition of nitrones and allenolates
Gonzalez-Cruz, David
Tejedor, David
de Armas, Pedro
Morales, Ezequiel Q.
Garcia-Tellado, Fernando
CHEMICAL COMMUNICATIONS, 2006, (26) : 2798 - 2800
[43] Synthesis of polymer[2]catenane by azide-alkyne Huisgen cycloaddition
Pangilinan, Katrina
Advincula, Rigoberto
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[44] A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study
Bahsis, Lahoucine
Ben El Ayouchia, Hicham
Anane, Hafid
Pascual-Alvarez, Alejandro
De Munno, Giovanni
Julve, Miguel
Stiriba, Salah-Eddine
APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (04)
[45] [3+2]CYCLOADDITION OF CHLORDIAZEPOXIDE WITH ISOCYANATES
ZINNER, G
BLASS, H
BEYERSDORF, J
ARCHIV DER PHARMAZIE, 1987, 320 (03) : 210 - 213
[46] POLYMER-SUPPORTED CATALYSTS .2. POLYMER-SUPPORTED RUTHENIUM ACETATE AS AN OLEFIN HYDROGENATION CATALYST
NICOLAIDES, CP
COVILLE, NJ
JOURNAL OF MOLECULAR CATALYSIS, 1984, 24 (03): : 375 - 387
[47] Amine-Catalyzed [3+2] Huisgen Cycloaddition Strategy for the Efficient Assembly of Highly Substituted 1,2,3-Triazoles
Wang, Lei
Peng, Shiyong
Danence, Lee Jin Tu
Gao, Yaojun
Wang, Jian
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (19) : 6088 - 6093
[48] Immobilized [Cu(cdsalMeen)] on silica gel: a highly efficient heterogeneous catalyst for 'Click' [3+2] Huisgen cycloaddition
Zarenezhad, Elham
Rad, Mohammad Navid Soltani
Behrouz, Somayeh
Esmaielzadeh, Sheida
Farjam, Mojtaba
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2017, 14 (02) : 509 - 519
[49] COPPER(I) COMPLEXES WITH 2,2'-BIQUINOXALYL
BARANOWSKA, I
CHEMIA ANALITYCZNA, 1986, 31 (5-6): : 851 - 857
[50] COPPER(II) COMPLEXES WITH 2,2'-DIHYDROXYCHALKONES
BIRADAR, NS
PATIL, BR
KULKARNI, VH
MONATSHEFTE FUR CHEMIE, 1976, 107 (01): : 251 - 257

← 1 2 3 4 5 →