4.6 Article

Visible-light-induced tandem difluoroalkylated spirocyclization of N-arylpropiolamides: access to C3-difluoroacetylated spiro[4,5]trienones

Journal

NEW JOURNAL OF CHEMISTRY
Volume 46, Issue 9, Pages 4470-4482

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2nj00131d

Keywords

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Funding

  1. Natural Science Foundation in Henan Province Department of Education [21A150016]
  2. Innovative Funds Plan of Henan University of Technology [2020ZKCJ29]
  3. Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology [2017RCJH08]
  4. Undergraduate Innovation and Entrepreneurship Training Program from the University in Henan Province [S202110463014]

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A visible-light-catalyzed difluoroacetylated spirocyclization reaction of N-arylpropiolamides with ethyl bromodifluoroacetate as a CF2CO2Et radical precursor is described. This approach enables the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, ipso-cyclization, and dearomatization processes, providing a straightforward route to synthesize CF2CO2Et-containing spiro[4.5]trienones in moderate to good yields.
A visible-light-catalyzed difluoroacetylated spirocyclization of N-arylpropiolamides with ethyl bromodifluoroacetate as a CF2CO2Et radical precursor is described. This approach allows the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, ipso-cyclization and dearomatization processes. This protocol affords a straightforward route to synthesize CF2CO2Et-containing spiro[4.5]trienones in moderate to good yields.

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