Palladium-Catalyzed Substitution of Allylic Fluorides

Authors


  • We thank Prof. Guy Lloyd-Jones (Bristol) for free exchange of information, and Johnson–Matthey for the loan of palladium salts. We thank a referee for comments that stimulated further experiments. Dr. Sophie Purser helped in the initial phases of the work. Support from the CRL Spectroscopy Facilities (Dr. T. D. W. Claridge) is gratefully acknowledged.

Abstract

As unusual substrates for the Tsuji–Trost allylation reaction, allylic fluorides are responsive to palladium-catalyzed substitution. Their activity towards this reaction fits in the series OCO2Me>OBz≫F≫OAc. The classic stereoretention mechanism that involves sequential inversions does not operate in this case. Several distinct cases are considered.

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