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Palladium-Catalyzed Enantioselective C(sp3)–H Fluorination
Controlling Pd(IV) Reductive Elimination Pathways Enables Pd(II)-Catalysed Enantioselective C(sp3)−H Fluorination.
Nat. Chem. 2018;
20 August 2018 (online)
Key wordspalladium catalysis - directing groups - fluorination - reductive elimination - inner-sphere pathway
The presence of a C–F bond uniquely affects the physical and biological characteristics of molecules. The authors have developed a new direct method for synthesizing chiral organofluorines by palladium-catalyzed C(sp3)–H fluorination. Appropriate choice of a chiral transient directing group is key to the selective formation of the desired C(sp3)–F bond rather than the undesired C(sp3)–O bond.
Several mechanistic studies indicated that the desired C(sp3)–H fluorination proceeds by an inner-sphere pathway, whereas the undesired C(sp3)–O formation occurs through an SN2-type mechanism.