Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones.

@article{Gerbino2012NucleophileOL,
  title={Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones.},
  author={Dar{\'i}o C. Gerbino and Daniel Augner and Nikolay K Slavov and Hans-G{\"u}nther Schmalz},
  journal={Organic letters},
  year={2012},
  volume={14 9},
  pages={2338-41}
}
The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm). 

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