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Platinum-catalyzed substitution of allylic fluorides

Benedetto, Elena, Keita, Massaba, Tredwell, Matthew, Hollingworth, Charlotte, Brown, John M. and Gouverneur, Veronique 2012. Platinum-catalyzed substitution of allylic fluorides. Organometallics 31 (4) , pp. 1408-1416. 10.1021/om201029m

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Abstract

Allyl fluorides are reactive toward Pt-catalyzed alkylation with malonate and likewise toward N- and O-nucleophiles under mild conditions. The reactivity of fluoride as a leaving group equals or exceeds that of the esters and carbonates commonly employed in allylic alkylation. The order of leaving-group ability with Pt catalysts was found to be F ≥ OCO2Me ≫ OBz ≥ OAc. This discouraged the application of platinum catalysts for the reverse reaction, fluorination of allylic substrates. Fluoride displacement involves predominant or complete retention of configuration in all the observed cases, and this was confirmed as a general feature of Pt catalysis, the stereochemical integrity being as high or higher as in Pd catalysis for the examples chosen.

Item Type: Article
Status: Published
Schools: Medicine
Publisher: American Chemical Society
ISSN: 0276-7333
Last Modified: 04 Jun 2019 11:00
URI: http://orca.cf.ac.uk/id/eprint/122198

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