Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrenes | Zendy

Eric P. A. Talbot | Zendy; Talita de A. Fernandes | Zendy; Jeffrey M. McKenna | Zendy; F. Dean Toste | Zendy

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Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrenes

Author(s) -

Eric P. A. Talbot,

Talita de A. Fernandes,

Jeffrey M. McKenna,

F. Dean Toste

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja412881j

Subject(s) - chemistry , selectfluor , palladium , catalysis , yield (engineering) , styrene , boronic acid , intermolecular force , fluoride , enantiomeric excess , combinatorial chemistry , enantioselective synthesis , enantiomer , organic chemistry , molecule , inorganic chemistry , copolymer , polymer , materials science , metallurgy

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.

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