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Origins of halogen effects in bioorthogonal sydnone cycloadditions. 2018
Huimin Tao, and
Fang Liu, and
Ruxin Zeng, and
Zhuzhou Shao, and
Lufeng Zou, and
Yang Cao, and
Jennifer M Murphy, and
K N Houk, and
Yong Liang
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China. yongliang@nju.edu.cn.
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.
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