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

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 increas...

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Published in:Chemical communications (Cambridge, England) England), 2018-11, Vol.54 (96), p.13499-13502
Main Authors: Yoshida, Suguru, Tanaka, Junko, Nishiyama, Yoshitake, Hazama, Yuki, Matsushita, Takeshi, Hosoya, Takamitsu
Format: Article
Language:English
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Aromatic compounds
Energy levels
NMR
Nuclear magnetic resonance
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description 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.
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subjects Aromatic compounds
Energy levels
NMR
Nuclear magnetic resonance
title Further enhancement of the clickability of doubly sterically-hindered aryl azides by para-amino substitution
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