Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: preparation of ortho-substituted cinnamates and biarylacetic acids.

@article{Costa2002SyntheticAO,
  title={Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: preparation of ortho-substituted cinnamates and biarylacetic acids.},
  author={Ana Costa and Carmen N{\'a}jera and Jos{\'e} Miguel Sansano},
  journal={The Journal of organic chemistry},
  year={2002},
  volume={67 15},
  pages={
          5216-25
        }
}
The synthetic applications of o-halobenzyl and p-halobenzyl sulfones as precursors of 1,3- and 1,5-zwitterionic synthons, respectively, are described. Their alpha-sulfonyl carbanions, generated by means of the phosphazene base P2-Et or BuLi or K2CO3 under PTC conditions, reacted with different electrophiles such as alkyl halides, aldehydes, and electrophilic olefins. Palladium-catalyzed cross-coupling processes such as Heck, Suzuki, and Sonogashira reactions can be efficiently performed at the… 
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