4.7 Article

A metal-free visible-light-promoted phosphorylation/cyclization reaction in water towards 3-phosphorylated benzothiophenes

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 7, Issue 14, Pages 1884-1889

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo00222d

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Funding

  1. Center of Advanced Analysis & Computational Science (Zhengzhou University)
  2. National Natural Science Foundation of China [21971224, 21802040]
  3. China Postdoctoral Science Foundation [2019M652561]
  4. Key Research Projects of Universities in Henan Province [19A350011, 20A150006]
  5. Henan Province Young Talents Elevation Program [2019HYTP023]

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A metal-free visible-light-induced 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN)-catalyzed phosphorylation/cyclization reaction was developed in water at room temperature for the synthesis of 3-phosphorylated benzothiophenes. Notably, the conventional organic solvents were avoided. More importantly, this silver-free system circumvents the generation of by-product benzo[b]phosphole oxides. With this strategy, a series of 3-phosphorylated benzothiophenes bearing various functional groups were synthesized in good to excellent yields.

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