Metal chelating systems synthesized using the copper(I) catalyzed azide-alkyne cycloaddition

被引：380

作者：

Struthers, Harriet ^{[1
]}

Mindt, Thomas L. ^{[2
]}

Schibli, Roger ^{[1
]}

机构：

[1] ETH, Dept Chem & Appl Biosci, Inst Pharmaceut Sci, CH-8093 Zurich, Switzerland

[2] Univ Basel Hosp, Div Radiol Chem, CH-4031 Basel, Switzerland

来源：

DALTON TRANSACTIONS | 2010年 / 39卷 / 03期

关键词：

CROSS-COUPLING REACTIONS; CHIRAL FERROCENYL PHOSPHINES; CLICK-TO-CHELATE; 1,3-DIPOLAR CYCLOADDITION; TERMINAL ALKYNES; IN-VITRO; GOLD NANOPARTICLES; STRUCTURAL-CHARACTERIZATION; RUTHENIUM(II) COMPLEXES; HUISGEN CYCLOADDITION;

D O I：

10.1039/b912608b

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The copper(I) catalyzed azide-alkyne cycloaddition (CuAAC) is the premier example of a click reaction. The reaction is modular, reliable and easy to perform, providing easy access to molecular diversity. The majority of reported applications of the reaction employ the 1,2,3-triazole as a stable linkage to connect two chemical/biological components, while the potential for metal coordination of the heterocycle itself has received much less attention. In fact, 1,4-functionalized 1,2,3-triazoles are versatile ligands offering several donor sites for metal coordination, including N3, N2 and C5. In this article, we summarize the areas in which the CuAAC has been applied to the synthesis of novel triazole-containing ligands for transition metals.

引用

页码：675 / 696

页数：22

共 144 条

[1] A novel organometallic aqua complex of technetium for the labeling of biomolecules:: Synthesis of [99mTc(OH2)3(CO)3]+ from [99mTcO4]- in aqueous solution and its reaction with a bifunctional ligand [J].

Alberto, R ;

Schibli, R ;

Egli, A ;

Schubiger, AP ;

Abram, U ;

Kaden, TA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (31) :7987-7988

[2] First application of fac-[99mTc(OH2)3(CO)3]+ in bioorganometallic chemistry:: Design, structure, and in vitro affinity of a 5-HT1A receptor ligand labeled with 99mTc [J].

Alberto, R ;

Schibli, R ;

Schubiger, AP ;

Abram, U ;

Pietzsch, HJ ;

Johannsen, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (25) :6076-6077

[3]

Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO

[4]

2-6

[5] Copper nanoparticles in click chemistry: an alternative catalytic system for the cycloaddition of terminal alkynes and azides [J].

Alonso, Francisco ;

Moglie, Yanina ;

Radivoy, Gabriel ;

Yus, Miguel .

TETRAHEDRON LETTERS, 2009, 50 (20) :2358-2362

[6] Base dependence in copper-catalyzed Huisgen reactions: Efficient formation of bistriazoles [J].

Angell, Yu ;

Burgess, Kevin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (20) :3649-3651

[7] Europium confined cyclen dendrimers with photophysically active triazoles [J].

Antoni, Per ;

Malkoch, Michael ;

Vamvounis, George ;

Nystrom, Daniel ;

Nystrom, Andreas ;

Lindgren, Mikael ;

Hult, Anders .

JOURNAL OF MATERIALS CHEMISTRY, 2008, 18 (22) :2545-2554

[8] Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry [J].

Aucagne, Vincent ;

Leigh, David A. .

ORGANIC LETTERS, 2006, 8 (20) :4505-4507

[9] Synthesis and coordination chemistry of ferrocenyl-1,2,3-triazolyl ligands [J].

Badeche, Sihem ;

Daran, Jean-Claude ;

Ruiz, Jaime ;

Astruc, Didier .

INORGANIC CHEMISTRY, 2008, 47 (11) :4903-4908

[10] Bifunctional single amino acid chelates for labeling of biomolecules with the {Tc(CO)3}+ and {Re(CO)3}+ cores.: Crystal and molecular structures of [ReBr(CO)3(H2NCH2C5H4N)], [Re(CO)3{(C5H4NCH2)2NH}]Br, [Re(CO)3{(C5H4NCH2)2NCH2CO2H}]Br, [Re(CO)3{X(Y)NCH2CO2CH2CH3}]Br (X = Y=2-pyridylmethyl; X=2-pyridyimethyl, Y=2-(1-methylimidazolyl)methyl; X = Y=2-(1-methylimidazolyl)methyl), [ReBr(CO)3{(C5H4NCH2)NH(CH2C4H3S)}], and [Re(CO)3{(C5H4NCH2)N(CH2C4H3S)(CH2CO2)}] [J].

Banerjee, SR ;

Levadala, MK ;

Lazarova, N ;

Wei, LH ;

Valliant, JF ;

Stephenson, KA ;

Babich, JW ;

Maresca, KP ;

Zubieta, J .

INORGANIC CHEMISTRY, 2002, 41 (24) :6417-6425

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