Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 4, Pages 1422-1426Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509748
Keywords
cycloparaphenylene; flow chemistry; lithiation; microfluidics; microreactors
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Funding
- National Research Foundation of Korea (NRF) - Korean government (MSIP) [2008-0061983]
- National Research Foundation of Korea [2008-0061983] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Cycloparaphenylene (CPP) has been recognized as an attractive template for the bottom-up synthesis of carbon nanotubes with uniform diameter, and is important for the chemistry of graphitic as well as ring-shaped macromolecules. However, the reported routes from halogenated benzenes have suffered from low yields even under time-and labor-consuming multistep conditions. Herein we report a flow-assisted synthesis of [10]CPP in four steps under mild conditions. For the synthesis, a selective nucleophilic addition of the unprotected diketone without the double-added byproduct was achieved within 3 s in high yield. Subsequently, the obtained compound was reacted with dilithiated benzene at 25 degrees C to form a U-shaped precursor for CPP in a separate microreactor, which was finally dimerized and aromatized to obtain [10]CPP by a two-step in-flask reaction. Precise control of time and flow facilitated by the flow-assisted system enabled the development of an efficient synthetic route for [10]CPP.
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