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Visible light amination/Smiles cascade: access to phthalazine derivatives.

Etienne BrachetLeyre MarzoMohamed SelktiBurkhard KönigPhilippe Belmont
Published in: Chemical science (2016)
We report the synthesis of various phthalazines via a new cascade reaction, initiated by visible light photocatalysis, involving a radical hydroamination reaction followed by a radical Smiles rearrangement. Phthalazine derivatives are obtained in high yields and from a broad scope readily accessible ortho-alkynylsulfonohydrazone precursors. The mild photoredox conditions ensure an excellent functional group tolerance. Application of this strategy to a one-pot protocol starting from the corresponding carbonyl compounds, and subsequent functionalization allow the rapid synthesis of structurally diverse structures.
Keyphrases
  • visible light
  • randomized controlled trial
  • structure activity relationship
  • high resolution
  • mass spectrometry
  • electron transfer
  • quantum dots