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Issue 40, 2018
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Origins of halogen effects in bioorthogonal sydnone cycloadditions

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Abstract

Halogen substituents increase sydnone cycloaddition reactivities substantially. Fluoro-sydnones are superior to bromo- and chloro-sydnones, and can achieve extremely high second-order rate constants with strained alkynes. Computational studies have revealed the fluorine substituent increases the reactivity of sydnone mainly by lowering its distortion energy.

Graphical abstract: Origins of halogen effects in bioorthogonal sydnone cycloadditions

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Article information


Submitted
16 Mar 2018
Accepted
23 Apr 2018
First published
23 Apr 2018

Chem. Commun., 2018,54, 5082-5085
Article type
Communication

Origins of halogen effects in bioorthogonal sydnone cycloadditions

H. Tao, F. Liu, R. Zeng, Z. Shao, L. Zou, Y. Cao, J. M. Murphy, K. N. Houk and Y. Liang, Chem. Commun., 2018, 54, 5082
DOI: 10.1039/C8CC02128G

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