Issue 40, 2018
From the journal:

Chemical Communications

Origins of halogen effects in bioorthogonal sydnone cycloadditions†

Huimin Tao, ORCID logo ‡a   Fang Liu, ORCID logo ‡a   Ruxin Zeng, ORCID logo a   Zhuzhou Shao, ORCID logo a   Lufeng Zou,b   Yang Cao,c   Jennifer M. Murphy,d   K. N. Houk ORCID logo *e  and  Yong Liang ORCID logo *a  

* Corresponding authors

a State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
E-mail: yongliang@nju.edu.cn

b Gaussian, Inc., Wallingford, Connecticut 06492, USA

c Institute of New Energy, Shenzhen 518031, China

d Crump Institute for Molecular Imaging, David Geffen School of Medicine, University of California, Los Angeles, California 90095, USA

e Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA
E-mail: houk@chem.ucla.edu

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

DOI
https://doi.org/10.1039/C8CC02128G
Article type
Communication
Submitted
16 Mar 2018
Accepted
23 Apr 2018
First published
23 Apr 2018

Chem. Commun., 2018,54, 5082-5085

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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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