Previous research by Furstner has shown that Fe(acac)3 catalyzed cross-coupling reactions between an aryl chloride and a Grignard reagent are most successful when the aryl chloride contains electron-deficient substituents1. Several Fe(acac)3 catalyzed cross-coupling reactions between various fluorinated aryl chlorides and 1-hexylmagnesium bromide were conducted in order to gather data on the effectiveness of fluorine at promoting the cross-coupling of an aryl group and a Grignard reagent. It was discovered that fluorine promotes the greatest coupling conversions when in the meta position to the chlorine. 4-chlorobenzaldehyde bis trifluoroethyl acetal was successfully synthesized. The trifluoroethyl acetal protecting group both prevented the aldehyde from reacting with the Grignard reagent and promoted nearly complete conversion to 4-n-hexylbenzaldehyde bis trifluoroethyl acetal. Thus, highly efficient cross-coupling between chlorobenzaldehyde derivatives and a Grignard reagent is now possible using this acetal. 1. Fuerstner, Alois, Andreas Leitner, Maria Mendez, and Helga Krause. "Iron-Catalyzed Cross-Coupling Reactions.." J. Am. Chem. Soc. (2003): 13856-13863. Print.

Cross-coupling reactions of fluorinated aryl chlorides and aryl chloride acetals with 1-hexylmagnesium bromide

249th National Meeting (2015)

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