4.7 Article

Copper-Catalyzed Selective Defluorinative Sulfuration of Trifluoropropanamides Leading to α-Fluorothioacrylamides

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 2, Pages 1591-1600

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02436

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Funding

  1. Natural Science Foundation of Guangxi Province [2018GXNSFDA281011]
  2. Plan Project of Wenzhou Municipal Science and Technology [ZG2019026]

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A practical and efficient method for synthesizing alpha-fluorothioacrylamide was developed through selective defluorinative sulfuration of trifluoropropanamides with disulfides. The N-chelation-assisted copper-catalyzed defluorination and sulfurization reactions show excellent functional group tolerance and incorporation of both sulfur atoms of disulfides into acrylamides.
A practical and efficient method for the synthesis of alpha-fluorothioacrylamide was developed from selective defluorinative sulfuration of trifluoropropanamides with disulfides. The N-chelation-assisted copper-catalyzed defluorination and sulfurization reactions feature excellent functional group tolerance and incorporation of both sulfur atoms of disulfides into acrylamides.

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