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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Bibliographic Details
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
Subjects:
Aromatic compounds
Energy levels
NMR
Nuclear magnetic resonance
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc05791e