4.7 Article

The aerobic oxidative hydroxysulfurization of gem-difluoroalkenes to produce α,α-difluoro-β-hydroxysulfides

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 20, Pages 5831-5836

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00676b

Keywords

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Funding

  1. National Natural Science Foundation of China [21572126, 21202095]
  2. Technicians Troop Construction Projects of Henan Province [C20150030]
  3. Program of Science and Technology Innovation Talents of Henan Province [184100510011]
  4. Natural Science Foundation of Henan Province [212300410379]
  5. Key Scientific and Technological Project of Henan Province [192102110222]

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The efficient aerobic oxidative hydroxysulfurization reaction developed in this study allows for the production of alpha,alpha-difluoro-beta-hydroxysulfides from gem-difluoroalkenes and aryl or alkyl thiols, demonstrating high levels of chemoselectivity and regioselectivity.
The efficient aerobic oxidative hydroxysulfurization of gem-difluoroalkenes with aryl or even alkyl thiols to produce alpha,alpha-difluoro-beta-hydroxysulfides has been developed. The reaction was found to display several advantageous attributes, including high levels of chemoselectivity and regioselectivity, moderate to excellent yields, broad substrate scope, and the ability to be scaled up in the absence of any transition metals or phosphine reductants. For this reason and due to its high efficiency, easy operation, and environmental safety, the reaction was deemed to conform to the ideology of green chemistry.

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