Reagent-Installed Capsule Network: Selective Thiocarbamoylation of Aromatic Amines in Crystals with Preinstalled CH3NCS

Authors

  • Dr. Yasuhide Inokuma,

    1. Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan)
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  • Guo-Hong Ning,

    1. Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan)
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  • Prof. Dr. Makoto Fujita

    Corresponding author
    1. Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan)
    • Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan)
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  • This research was supported by the CREST project of the Japan Science and Technology Agency (JST), for which M.F. is the principal investigator, and also in part by KAKENHI (20044006), JSPS, and Global COE Program (Chemistry Innovation through Cooperation of Science and Engineering), MEXT (Japan). Y.I. thanks Kurata Grants for younger scientists.

Abstract

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Crystalline reagent capsules were prepared by installing CH3NCS into networked molecular capsules. While the tight encapsulation completely prevented leaching of reagent molecules into the supernatant, introduction of amines into the interstitial pores triggered reagent delivery. As a result, enhanced substrate selectivity was observed in crystalline-state thiocarbamoylation (see picture; 86:14 in favor of 2- vs. 1-naphthylamine).

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