1541177-39-2Relevant academic research and scientific papers
A continuous-flow approach to 3,3,3-trifluoromethylpropenes: Bringing together grignard addition, peterson elimination, inline extraction, and solvent switching
Hamlin, Trevor A.,Lazarus, Gillian M. L.,Kelly, Christopher B.,Leadbeater, Nicholas E.
, p. 1253 - 1258 (2014)
A continuous-flow approach to the synthesis of 3,3,3-trifluoromethylpropenes involving Grignard addition of (trimethylsilyl)methylmagnesium chloride to a trifluoromethyl ketone followed by dehydrative desilylation of the α-tri fluoromethyl-β-hydroxysilyl alcohol using trimethylsilyl tri fluoromethanesulfonate is reported. An inline aqueous/organic extraction and a concomitant solvent switch were key to the success of the methodology. Transition from batch to continuous flow conditions allows for higher yields, shorter reaction times, and facile scale out.
Methylenation of perfluoroalkyl ketones using a Peterson olefination approach
Hamlin, Trevor A.,Kelly, Christopher B.,Cywar, Robin M.,Leadbeater, Nicholas E.
, p. 1145 - 1153 (2014/03/21)
An operationally simple, inexpensive, and rapid route for the olefination of a wide array of trifluoromethyl ketones to yield 3,3,3- trifluoromethylpropenes is reported. Using a Peterson olefination approach, the reaction gives good to excellent yields of the alkene products and can be performed without purification of the β-hydroxysilyl intermediate. The reaction can be extended to other perfluoroalkyl substituents and is easily scaled up. The alkenes prepared can be readily transformed into a variety of other perfluoroalkyl-containing compounds.
