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. 2014 Apr 14;53(16):4181-5.
doi: 10.1002/anie.201310056. Epub 2014 Mar 18.

cis-Specific hydrofluorination of alkenylarenes under palladium catalysis through an ionic pathway

Enrico Emer  1 , Lukas Pfeifer, John M Brown, Véronique Gouverneur
Affiliations

cis-Specific hydrofluorination of alkenylarenes under palladium catalysis through an ionic pathway

Enrico Emer et al. Angew Chem Int Ed Engl. .

Abstract

This paper describes the hydrofluorination of alkenes through sequential H(-) and F(+) addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed.

Keywords: catalysis; fluorine; palladium; regioselectivity; stereospecificity.

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