6533b858fe1ef96bd12b57b1

RESEARCH PRODUCT

A new strategy for the synthesis of highly functionalised fluorinated compounds by reaction of lithium dianions of carboxylic acids with perfluoroketene dithioacetals

Jean-philippe BouillonSalvador GilMargarita ParraEnrique SotocaEnrique SotocaCharles Portella

subject

chemistry.chemical_compoundTrifluoromethylchemistryOrganic ChemistryDrug DiscoverySynthonchemistry.chemical_elementLithiumBiochemistryMedicinal chemistryFluoride

description

The reaction of perfluoroketene dithioacetal with lithium dienediolates of carboxylic acids proceeds at the ω position probably through an addition to the π system followed by elimination of the vinylic fluoride. The preparative value of this reaction depends strongly on the reaction and work-up conditions. The overall process lead to highly functionalised synthons containing a trifluoromethyl group.

https://doi.org/10.1016/j.tet.2005.02.082