93359-83-2Relevant articles and documents
Palladium-catalyzed substitution and cross-coupling of benzylic fluorides
Blessley, George,Holden, Patrick,Walker, Matthew,Brown, John M.,Gouverneur, Veronique
supporting information; experimental part, p. 2754 - 2757 (2012/07/16)
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 ≈ p-NO2C6H 4CO2 ≈ OCO2CH3 > F > CH3CO2, a ranking similar to allylic fluorides under Pd catalysis.
