Efficient synthesis of a labile copper(I)-rotaxane complex using click chemistry

被引：89

作者：

Mobian, Pierre ^{[1
]}

Collin, Jean-Paul ^{[1
]}

Sauvage, Jean-Pierre ^{[1
]}

机构：

[1] Univ Strasbourg 1, CNRS, UMR 7177, Fac Chim, F-67070 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 28期

关键词：

rotaxane; click chemistry;

D O I：

10.1016/j.tetlet.2006.05.024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(I)-induced threading of 5,5'-diazidomethyl-2,2'-bipyridine through a coordinating ring followed by reaction of a propargyl ether attached to a stopper group leads to the desired rotaxane in 62% yield. The reaction is carried out under the 'click chemistry' conditions with 0.75 equiv of additional copper(I). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4907 / 4909

页数：3

共 34 条

[1]

[Anonymous], 2001, ACC CHEM RES, V34

[2] 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

[3]

Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO

[4]

2-X

[5] Molecular machines [J].

Balzani, V ;

Gómez-López, M ;

Stoddart, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (07) :405-414

[6]

Balzani V., 2003, Molecular Devices and Machines, a Journey into the Nanoworld

[7] Synthesis of a mechanically linked oligo[2]rotaxane [J].

Belaissaoui, A ;

Shimada, S ;

Ohishi, A ;

Tamaoki, N .

TETRAHEDRON LETTERS, 2003, 44 (11) :2307-2310

[8] 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

[9] Molecular shuttles by the protecting group approach [J].

Cao, JG ;

Fyfe, MCT ;

Stoddart, JF ;

Cousins, GRL ;

Glink, PT .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :1937-1946

[10] Information storage using supramolecular surface patterns [J].

Cavallini, M ;

Biscarini, F ;

Léon, S ;

Zerbetto, F ;

Bottari, G ;

Leigh, DA .

SCIENCE, 2003, 299 (5606) :531-531

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