Synfacts 2018; 14(09): 0931
DOI: 10.1055/s-0037-1609920
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Enantioselective C(sp3)–H Fluorination

Hisashi Yamamoto
Takahiro Sawano
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(sp3)−H Fluorination.

Nat. Chem. 2018;
10: 755-762
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20. August 2018 (online)



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.