An Inorganic Click Reaction for the Synthesis of Interlocked Molecules |
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Authors: | Alex Mapp Jamie T Wilmore Prof Dr Paul D Beer Prof Dr Jose M Goicoechea |
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Institution: | 1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Rd., Oxford, OX1 3TA UK;2. Department of Chemistry, Indiana University, 800 East Kirkwood Ave., Bloomington, IN, 47405 USA |
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Abstract: | We describe the use of the cyaphide-azide 1,3-dipolar cycloaddition reaction for the synthesis of a new class of inorganic rotaxanes containing gold(I) triazaphosphole stoppers. Electron-deficient bis-azides, which thread perethylated pillar5]arene in aromatic solvents, readily react with two equivalents of Au(IDipp)(CP) (IDipp=1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene) to afford interlocked molecules via an inorganic click reaction. These transformations proceed in good yields (ca. 65 %) and in the absence of a catalyst. The resulting organometallic rotaxanes are air- and moisture-stable and can be purified by column chromatography under aerobic conditions. The targeted rotaxanes were characterized by multi-element nuclear magnetic resonance (NMR) spectroscopy, mass-spectrometry, and single-crystal X-ray diffraction. |
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Keywords: | Azide Click Chemistry Cyaphide Rotaxanes Triazaphospholes |
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