Park H.
Verma P.
Hong K.
Yu J.-Q.
* The Scripps Research Institute, La Jolla, USA
Controlling Pd(IV) Reductive Elimination Pathways Enables Pd(II)-Catalysed Enantioselective
C(sp
3)−H Fluorination.
Nat. Chem. 2018;
10: 755-762
Key words
palladium catalysis - directing groups - fluorination - reductive elimination - inner-sphere
pathway
Significance
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.
Comment
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.
