Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones: A Rapid Click Reaction

Digvijay Gahtory; Rickdeb Sen; Andriy R. Kuzmyn; Jorge Escorihuela; Han Zuilhof

doi:10.1002/anie.201800937

Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones: A Rapid Click Reaction

Digvijay Gahtory, Rickdeb Sen, Andriy R. Kuzmyn, Jorge Escorihuela, Han Zuilhof^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

38 Citations (Scopus)

Abstract

Novel click reactions are of continued interest in fields as diverse as bio-conjugation, polymer science and surface chemistry. Qualification as a proper "click" reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain-promoted cycloaddition between cyclopropenes and o-quinones in solution and on a surface. We demonstrate the "click character" of the reaction in solution and on surfaces for both monolayer and polymer brush functionalization.

Original language	English
Pages (from-to)	10118-10122
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	32
Early online date	1 Jan 2018
DOIs	https://doi.org/10.1002/anie.201800937
Publication status	Published - 6 Aug 2018

Keywords

Kinetics
Mass spectrometry
Metal-free click reactions
Monolayers
Polymer brushes

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10.1002/anie.201800937Licence: CC BY-NC-ND

https://edepot.wur.nl/448755Licence: CC BY-NC-ND

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AU - Gahtory, Digvijay

AU - Sen, Rickdeb

AU - Kuzmyn, Andriy R.

AU - Escorihuela, Jorge

AU - Zuilhof, Han

PY - 2018/8/6

Y1 - 2018/8/6

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AB - Novel click reactions are of continued interest in fields as diverse as bio-conjugation, polymer science and surface chemistry. Qualification as a proper "click" reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain-promoted cycloaddition between cyclopropenes and o-quinones in solution and on a surface. We demonstrate the "click character" of the reaction in solution and on surfaces for both monolayer and polymer brush functionalization.

KW - Kinetics

KW - Mass spectrometry

KW - Metal-free click reactions

KW - Monolayers

KW - Polymer brushes

U2 - 10.1002/anie.201800937

DO - 10.1002/anie.201800937

M3 - Article

AN - SCOPUS:85045735898

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JF - Angewandte Chemie - International Edition

IS - 32

ER -

Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones: A Rapid Click Reaction

Abstract

Keywords

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