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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

Contributor(s):
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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Further Information

Publication History

Publication Date:
20 August 2018 (online)

 
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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.


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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.


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