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Further enhancement of the clickability of doubly sterically-hindered aryl azides by para-amino substitution

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Abstract

Introduction of an amino group at the para position of doubly sterically-hindered aryl azides significantly enhances the reactivity with cyclooctynes. The distortability of the azido group is synergistically enhanced by the para-electron-donating group and two bulky ortho substituents, which increases the HOMO energy level and provoke the steric inhibition of resonance, respectively.

Graphical abstract: Further enhancement of the clickability of doubly sterically-hindered aryl azides by para-amino substitution

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Publication details

The article was received on 17 Jul 2018, accepted on 12 Oct 2018 and first published on 15 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC05791E
Citation: Chem. Commun., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Further enhancement of the clickability of doubly sterically-hindered aryl azides by para-amino substitution

    S. Yoshida, J. Tanaka, Y. Nishiyama, Y. Hazama, T. Matsushita and T. Hosoya, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC05791E

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