High yielding synthesis of 2,2′-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes

被引：67

作者：

Lewis, J. E. M. ^{[1
]}

Bordoli, R. J. ^{[2
]}

Denis, M. ^{[1
]}

Fletcher, C. J. ^{[1
]}

Galli, M. ^{[1
]}

Neal, E. A. ^{[2
]}

Rochette, E. M. ^{[1
]}

Goldup, S. M. ^{[1
]}

机构：

[1] Univ Southampton, Chem, Southampton SO17 1BJ, Hants, England

[2] Queen Mary Univ London, Sch Biol & Chem Sci, Mile End Rd, London E1 4NS, England

来源：

CHEMICAL SCIENCE | 2016年 / 7卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

ACTIVE-TEMPLATE SYNTHESIS; SWITCHABLE MOLECULAR SHUTTLES; PHOTOPHYSICAL PROPERTIES; ARYL HALIDES; POLYAMINE MACROCYCLES; DIRECTED SYNTHESIS; CRYSTAL-STRUCTURE; TERMINAL ALKYNES; EFFICIENT METHOD; LIGANDS;

D O I：

10.1039/c6sc00011h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present an operationally simple approach to 2,2'-bipyridine macrocycles. Our method uses simple starting materials to produce these previously hard to access rotaxane precursors in remarkable yields (typically >65%) across a range of scales (0.1-5 mmol). All of the macrocycles reported are efficiently converted (>90%) to rotaxanes under AT-CuAAC conditions. With the requisite macrocycles finally available in sufficient quantities, we further demonstrate their long term utility through the first gram-scale synthesis of an AT-CuAAC [2] rotaxane and extend this powerful methodology to produce novel Sauvage-type molecular shuttles.

引用

页码：3154 / 3161

页数：8

共 137 条

[21] An Efficient Approach to Mechanically Planar Chiral Rotaxanes [J].

Bordoli, Robert J. ;

Goldup, Stephen M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (13) :4817-4820

[22] A C2-SYMMETRICAL CHIRAL 2,2'-BIPYRIDINE DERIVED FROM TARTARIC ACID [J].

BOTTEGHI, C ;

SCHIONATO, A ;

DELUCCHI, O .

SYNTHETIC COMMUNICATIONS, 1991, 21 (17) :1819-1823

[23] Lanthanide Directed Self-Assembly of Highly Luminescent Supramolecular "Peptide" Bundles from a-Amino Acid Functionalized 2,6-Bis(1,2,3-triazol-4-yl)pyridine (btp) Ligands [J].

Byrne, Joseph P. ;

Kitchen, Jonathan A. ;

O'Brien, John E. ;

Peacock, Robert D. ;

Gunnlaugsson, Thorfinnur .

INORGANIC CHEMISTRY, 2015, 54 (04) :1426-1439

[24] The btp [2,6-bis(1,2,3-triazol-4-yl[pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry [J].

Byrne, Joseph P. ;

Kitchen, Jonathan A. ;

Gunnlaugsson, Thorfinnur .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (15) :5302-5325

[25] Synthesis, structural, photophysical and electrochemical studies of various d-metal complexes of btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] ligands that give rise to the formation of metallo-supramolecular gels [J].

Byrne, Joseph P. ;

Kitchen, Jonathan A. ;

Kotova, Oxana ;

Leigh, Vivienne ;

Bell, Alan P. ;

Boland, John J. ;

Albrecht, Martin ;

Gunnlaugsson, Thorfinnur .

DALTON TRANSACTIONS, 2014, 43 (01) :196-209

[26] A Simple and Highly Effective Ligand System for the Copper(I)Mediated Assembly of Rotaxanes [J].

Campbell, Christopher J. ;

Leigh, David A. ;

Vitorica-Yrezabal, Inigo J. ;

Woltering, Steffen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) :13771-13774

[27] Heterolytic Activation of H2 Using a Mechanically Interlocked Molecule as a Frustrated Lewis Base [J].

Caputo, Christopher B. ;

Zhu, Kelong ;

Vukotic, V. Nicholas ;

Loeb, Stephen J. ;

Stephan, Douglas W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (03) :960-963

[28] The first synthesis of simplified 16- and 17-membered ring macropolypeptides containing the phenyl-indole system of Kistamycin and Chloropeptin I, II [J].

Carbonnelle, AC ;

Zamora, EG ;

Beugelmans, R ;

Roussi, G .

TETRAHEDRON LETTERS, 1998, 39 (25) :4471-4472

[29] SYNTHESIS OF MACROCYCLIC-COMPOUNDS CONTAINING 2 SEPARATE AND DISTINCT COORDINATING FRAGMENTS, 2,2'-BIPYRIDYL AND 2,9-DIPHENYL-1,10-PHENANTHROLINE [J].

CHAMBRON, JC ;

SAUVAGE, JP .

TETRAHEDRON, 1987, 43 (05) :895-904

[30]

Cheng CY, 2015, NAT NANOTECHNOL, V10, P547, DOI [10.1038/nnano.2015.96, 10.1038/NNANO.2015.96]

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