4.8 Article

Photocatalytic Cyclization/Defluorination Domino Sequence to Access 3-Fluoro-1,5-dihydro-2H-pyrrol-2-one Scaffold

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ORGANIC LETTERS
卷 23, 期 12, 页码 4754-4758

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01477

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资金

  1. National Natural Science Foundation of China [22078370, 21776318, 22078369, 81703365, 22003077]
  2. Basic Science Center Project for National Natural Science Foundation of China [72088101]
  3. Natural Science Foundation of Hunan Province [2018JJ3868, 2020JJ4682]
  4. Fundamental Research Funds for Central South University [2020zzts401]
  5. Central South University
  6. Theory and Application of Resource and Environment Management in the Digital Economy Era)

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In this study, an unprecedented photoinduced cyclization/defluorination domino process of N-allylbromodi-fluoroacetamide with cyclic secondary amines was reported, leading to the facile preparation of valuable 3-fluoro-1,5-dihydro-2H-pyrrol-2-ones from readily available starting materials under mild conditions. Preliminary mechanistic investigations suggest that a radical chain propagation and amine-promoted defluorination pathway are presumably involved in this transformation.
We herein report an unprecedented photoinduced cyclization/defluorination domino process of N-allylbromodi-fluoroacetamide with cyclic secondary amines. Consequently, a wide array of valuable 3-fluoro-1,5-dihydro-2H-pyrrol-2-ones were facilely prepared from readily available starting materials under mild conditions. Preliminary mechanistic investigations suggest that a radical chain propagation and amine-promoted defluorination pathway are presumably involved in this transformation.

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