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Fluoroiodomethane: A versatile CH2F Source

Fluoroiodomethane (FCH2I, CAS 373-53-5) is a liquid (bp 53.48C) that is easy to manipulate and useful as a precursor of the fluoromethyl (CH2F) unit. This C1 building block features different reactivity for the two carbon halogen bonds: accordingly, the



https://doi.org/10.1071/CH18045

Serena Monticelli
A and Vittorio PaceA,B
ADepartment of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, A-1090
Vienna, Austria.
B
Manuscript received: 29 January 2018.
Manuscript accepted: 11 April 2018.
Published online: 7 May 2018.

Vittorio Pace received his Ph.D. in Chemical Sciences from the Complutense University of Madrid in 2010. After post-doctoral training at Vienna, Manchester, and Stockholm, he
obtained a tenure track position at the University of Vienna. In 2016 he received the Habilitation in Pharmaceutical Chemistry from the University of Vienna and in 2017 the
Habilitation for Full Professor of Organic Chemistry.



Background
Fluoroiodomethane (FCH2I, CAS 373-53-5) is a liquid (bp 53.48C) that is easy to
manipulate and useful as a precursor of the fluoromethyl (CH2F) unit. This C1 building
block features different reactivity for the two carbon halogen bonds: accordingly, the

CH2–I linkage can be conveniently used for accomplishing nucleophilic substitution,
[1]


iodine–metal exchange, or transition-metal catalysed processes, leaving the fluor-
omethyl motif intact.Fluoromethylation of Aromatic Rings
In 2015, Hu reported the first example of a straightforward palladium-catalysed direct
monofluoromethylation of aryl boronic esters having ICH2F as the fluoromethyl donor
unit (Scheme 1).
[2]
The protocol is particularly attractive because of the mild reactionconditions and the very good functional group tolerance. In this sense, Hu’s procedure


improved previous work by Suzuki, which involved the preparation of benzyl fluoride
using pinacolboronate (40 equiv.) and stoichiometric palladium.
[3]



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