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J Org Chem. 2006 Jan 6;71(1):360-3.

Improved Julia-Kocienski conditions for the methylenation of aldehydes and ketones.

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  • Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany. aissa@mpi-muelheim.mpg.de


[reaction: see text] The scope of the methylenation of aldehydes and ketones under optimized Julia-Kocienski conditions is broadened by using 1-tert-butyl-1H-tetrazol-5-ylmethyl sulfone. Two different Barbier-type procedures are applied with NaHMDS at -78 degrees C or Cs2CO3 at 70 degrees C. The latter conditions are also adapted for the preparation of 1,2-disubstituted olefins and intramolecular olefination reactions.

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