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J Am Chem Soc. 2014 Mar 19;136(11):4101-4. doi: 10.1021/ja412881j. Epub 2014 Mar 11.

Asymmetric palladium-catalyzed directed intermolecular fluoroarylation of styrenes.

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1
Novartis Institutes for Biomedical Research , Horsham,West Sussex, RH12 5AB, United Kingdom.

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.

PMID:
24617344
PMCID:
PMC3971964
DOI:
10.1021/ja412881j
[Indexed for MEDLINE]
Free PMC Article
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