Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides

[摘要]：Benzylic fluorides are suitable substrates for Pd(0)-catalyzed Tsuji-Trost substitution using carbon, nitrogen, oxygen, and sulfur nucleophiles and for cross-coupling with phenylboronic acid. For the bifunctional substrate 4-chlorobenzyl fluoride, fine-tuning of the reaction conditions allows for the regioselective displacement of either the chlorine or fluorine substituent. The leaving group ability of fluoride vs other groups displaced in substitution is CF3CO2 approximate to p-NO2C6H4CO2 approximate to OCO2CH3 > F > CH3CO2, a ranking similar to allyllc fluorides under Pd catalysis.

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