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Recent Advances in the Chemistry of Fluorine-Containing π-Allylmetal and Allenylmetal Complexes

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π-Allylmetal complexes derived from α-fluoroalkylated allyl mesylates react smoothly with various nucleophiles such as stabilized carbanions, carboxylates, and amines at the carbon distal to a fluoroalkyl group in a highly regioselective manner to give the corresponding γ-products in high to excellent yields. Treatment of the above fluorine-containing π-allylmetal complexes with hydride nucleophile gives the adducts derived from the hydride attacking on the carbon attached to a fluoroalkyl group. The γ-adducts, obtained by the reaction of π-allylpalladium complex with α-methoxy acetate or N-protected glycine, undergo smooth Ireland-Claisen rearrangement to give the corresponding multifunctionalized molecules in high yields. On the other hand, the reaction of α- fluoroalkylated propargylic mesylates with zinc reagents or stabilized carbanions in the presence of palladium catalyst affords fluorine-containing allene or furan derivatives respectively, in high yields, via allenylpalladium complex.

Keywords: Ireland-Claisen rearrangement; bidentate ligand; electron-withdrawing effect; fluoroalkylated complexes; lithionitromethane; molybdenum-catalyzed reaction; nucleophiles; organofluorine chemistry

Document Type: Research Article

Affiliations: Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.

Publication date: January 1, 2006


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