A metal-complex-tolerant CuAAC 'click' protocol exemplified through the preparation of homo- and mixed-metal-coordinated [2]rotaxanes

被引：41

作者：

Cabrera, Diego Gonzalez ^{[1
]}

Koivisto, Bryan D. ^{[1
]}

Leigh, David A. ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

CHEMICAL COMMUNICATIONS | 2007年 / 41期

关键词：

D O I：

10.1039/b713501g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of mono- and bis-metallated [ 2] rotaxanes has been prepared using a CuAAC `click' protocol that is compatible with metal-coordinated building blocks and ligands; the methodology provides a general means for appending a metal ion or complex to an organic scaffold via Cu(I)-catalysed `click' chemistry, even when the molecule contains redox-active or kinetically labile metals or vacant ligand sites.

引用

页码：4218 / 4220

页数：3

共 36 条

[1] Long-range electron transfer in porphyrin-containing [2]-rotaxanes:: Tuning the rate by metal cation coordination [J].

Andersson, M ;

Linke, M ;

Chambron, JC ;

Davidsson, J ;

Heitz, V ;

Hammarström, L ;

Sauvage, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4347-4362

[2] Porphyrin-containing [2]-rotaxanes:: Metal coordination enhanced superexchange electron transfer between noncovalently linked chromophores [J].

Andersson, M ;

Linke, M ;

Chambron, JC ;

Davidsson, J ;

Heitz, V ;

Sauvage, JP ;

Hammarström, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3526-3527

[3] Catalytic "click" rotaxanes:: A substoichiometric metal-template pathway to mechanically interlocked architectures [J].

Aucagne, V ;

Hänni, KD ;

Leigh, DA ;

Lusby, PJ ;

Walker, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2186-2187

[4] Catalytic "Active-Metal" template synthesis of [2]rotaxanes, [3]rotaxanes, and molecular shuttles, and some observations on the mechanism of the Cu(I)-catalyzed azide-alkyne 1,3-cycloaddition [J].

Aucagne, Vincent ;

Berna, Jose ;

Crowley, James D. ;

Goldup, Stephen M. ;

Haenni, Kevin D. ;

Leigh, David A. ;

Lusby, Paul J. ;

Ronaldson, Vicki E. ;

Slawin, Alexandra M. Z. ;

Viterisi, Aurlien ;

Walker, D. Barney .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :11950-11963

[5]

Ball P, 2007, CHEM WORLD-UK, V4, P46

[6] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[7] From reactants to products via simple hydrogen-bonding networks: Information transmission in chemical reactions [J].

Brancato, G ;

Coutrot, F ;

Leigh, DA ;

Murphy, A ;

Wong, JKY ;

Zerbetto, F .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (08) :4967-4971

[8] Convenient methods for the synthesis of ferrocene-carbohydrate conjugates [J].

Casas-Solvas, JM ;

Vargas-Berenguel, A ;

Capitán-Vallvey, LF ;

Santoyo-González, F .

ORGANIC LETTERS, 2004, 6 (21) :3687-3690

[9] Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].

Chan, TR ;

Hilgraf, R ;

Sharpless, KB ;

Fokin, VV .

ORGANIC LETTERS, 2004, 6 (17) :2853-2855

[10] Beyond switches: Ratcheting a particle energetically uphill with a compartmentalized molecular machine [J].

Chatterjee, MN ;

Kay, ER ;

Leigh, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :4058-4073

← 1 2 3 4 →