Cadiot-Chodkiewicz active template synthesis of rotaxanes and switchable molecular shuttles with weak intercomponent interactions

被引:92
作者
Berna, Jose [1 ]
Goldup, Stephen M. [1 ]
Lee, Ai-Lan [1 ]
Leigh, David A. [1 ]
Symes, Mark D. [1 ]
Teobaldi, Gilberto [2 ]
Zerbetto, Francesco [2 ]
机构
[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
[2] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
Cadiot-Chodkiewicz reaction; heterocoupling; molecular shuttles; rotaxanes; template synthesis;
D O I
10.1002/anie.200800891
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Shuttling fast and loose: Weak interaction, switchable, rotaxane-based molecular shuttles, in which the positional fidelity of the macrocycle is conferred by a single hydrogen bond in each state, are constructed through the high-yielding and selective active template heterocoupling of different functionalized alkynes using the Cadiot-Chodkiewicz reaction. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4392 / 4396
页数:5
相关论文
共 60 条
  • [1] A convenient route to unsymmetrical conjugated diynes
    Alami, M
    Ferri, F
    [J]. TETRAHEDRON LETTERS, 1996, 37 (16) : 2763 - 2766
  • [2] Remarkable positional discrimination in bistable light- and heat-switchable hydrogen-bonded molecular shuttles
    Altieri, A
    Bottari, G
    Dehez, F
    Leigh, DA
    Wong, JKY
    Zerbetto, F
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (20) : 2296 - 2300
  • [3] Altieri A., 2003, ANGEW CHEM, V115, P2398
  • [4] Interlocked and intertwined structures and superstructures
    Amabilino, DB
    Stoddart, JF
    [J]. CHEMICAL REVIEWS, 1995, 95 (08) : 2725 - 2828
  • [5] A MOLECULAR SHUTTLE
    ANELLI, PL
    SPENCER, N
    STODDART, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) : 5131 - 5133
  • [6] Acid-base controllable molecular shuttles
    Ashton, PR
    Ballardini, R
    Balzani, V
    Baxter, I
    Credi, A
    Fyfe, MCT
    Gandolfi, MT
    Gómez-López, M
    Martínez-Díaz, MV
    Piersanti, A
    Spencer, N
    Stoddart, JF
    Venturi, M
    White, AJP
    Williams, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (46) : 11932 - 11942
  • [7] Catalytic "click" rotaxanes:: A substoichiometric metal-template pathway to mechanically interlocked architectures
    Aucagne, V
    Hänni, KD
    Leigh, DA
    Lusby, PJ
    Walker, DB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) : 2186 - 2187
  • [8] 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
    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
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) : 11950 - 11963
  • [9] A molecular elevator
    Badjic, JD
    Balzani, V
    Credi, A
    Silvi, S
    Stoddart, JF
    [J]. SCIENCE, 2004, 303 (5665) : 1845 - 1849
  • [10] Operating molecular elevators
    Badjic, JD
    Ronconi, CM
    Stoddart, JF
    Balzani, V
    Silvi, S
    Credi, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) : 1489 - 1499