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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.

Original publication

DOI

10.1002/anie.201310056

Type

Journal article

Journal

Angew Chem Int Ed Engl

Publication Date

14/04/2014

Volume

53

Pages

4181 - 4185

Keywords

catalysis, fluorine, palladium, regioselectivity, stereospecificity