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Asymmetric palladium-catalyzed directed intermolecular fluoroarylation of styrenes.

ABSTRACT: A mild catalytic asymmetric direct fluoro-arylation of styrenes has been developed. The palladium-catalyzed three-component coupling of Selectfluor, a styrene and a boronic acid, provides chiral monofluorinated compounds in good yield and in high enantiomeric excess. A mechanism proceeding through a Pd(IV)-fluoride intermediate is proposed for the transformation and synthesis of an sp(3) C-F bond.

SUBMITTER: Talbot EP

PROVIDER: S-EPMC3971964 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Asymmetric palladium-catalyzed directed intermolecular fluoroarylation of styrenes.

Talbot Eric P A EP Fernandes Talita de A Tde A McKenna Jeffrey M JM Toste F Dean FD

Journal of the American Chemical Society 20140311 11

A mild catalytic asymmetric direct fluoro-arylation of styrenes has been developed. The palladium-catalyzed three-component coupling of Selectfluor, a styrene and a boronic acid, provides chiral monofluorinated compounds in good yield and in high enantiomeric excess. A mechanism proceeding through a Pd(IV)-fluoride intermediate is proposed for the transformation and synthesis of an sp(3) C-F bond. ...[more]

PMID: 24617344

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