4.7 Article

Origins of halogen effects in bioorthogonal sydnone cycloadditions

Journal

CHEMICAL COMMUNICATIONS
Volume 54, Issue 40, Pages 5082-5085

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8cc02128g

Keywords

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Funding

  1. National Thousand Young Talents Program in China
  2. Jiangsu Specially-Appointed Professor Plan in China
  3. NSF of Jiangsu Province in China [BK20170631]
  4. National Institute of General Medical Sciences, National Institutes of Health [R01 GM109078]
  5. Shenzhen Peacock Plan [1208040050847074]
  6. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM109078] Funding Source: NIH RePORTER

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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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