Palladium-Catalyzed Enantioselective C(sp3)–H Fluorination

Hisashi Yamamoto; Takahiro Sawano

doi:10.1055/s-0037-1609920

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Synfacts 2018; 14(09): 0931
DOI: 10.1055/s-0037-1609920

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Palladium-Catalyzed Enantioselective C(sp³)–H Fluorination

Rezensent(en):

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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Publikationsverlauf

Publikationsdatum:
20. August 2018 (online)

Abstract
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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 S_N2-type mechanism.

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