4.3 Article

Radical coupling of arylthiodifluoroacetic acids and ethynylbenziodoxolone (EBX) reagents to access arylthiodifluoromethylated alkynes

期刊

JOURNAL OF FLUORINE CHEMISTRY
卷 242, 期 -, 页码 -

出版社

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2020.109715

关键词

Radical coupling; Decarboxylation; Arylthiodifluoroacetic acid; Ethynylbenziodoxolone (EBX) reagent; Transition-metal-free; Alkyne

资金

  1. National Natural Science Foundation of China [21421002, 21991211]
  2. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]

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An efficient radical coupling method for arylthiodifluoroacetic acids and ethynylbenziodoxolone (EBX) reagents has been developed, providing moderate to good yields of ArSCF2-substituted alkynes. The synthetic utility of this protocol was demonstrated by transforming the resulting products into other ArSCF2-substituted alkynes and alkenes.
A practical and efficient radical coupling of easily available arylthiodifluoroacetic acids and ethynylbenziodoxolone (EBX) reagents has been reported. Under transition metal-free conditions, aryl-substituted EBXs were converted to the corresponding ArSCF2-substituted alkynes in moderate to good yields, whereas TIPS-EBX underwent silver-catalyzed decarboxylative conditions to deliver the desired coupling products. The synthetic utility of this protocol was demonstrated through the transformation of resulting product to other ArSCF2 substituted alkynes and alkenes.

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