ol7b02522_si_001.pdf (11.03 MB)
Download fileEx Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates
journal contribution
posted on 2017-09-13, 14:36 authored by Cedrick Veryser, Joachim Demaerel, Vidmantas Bieliu̅nas, Philippe Gilles, Wim M. De BorggraeveA convenient transformation
of phenols into the corresponding aryl
fluorosulfates is presented: the first protocol to completely circumvent
direct handling of gaseous sulfuryl fluoride (SO2F2). The proposed method employs 1,1′-sulfonyldiimidazole
as a precursor to generate near-stoichiometric amounts of SO2F2 gas using a two-chamber reactor. With NMR studies,
it was shown that this ex situ gas evolution is extremely
rapid, and a variety of phenols and hydroxylated heteroarenes were
fluorosulfated in good to excellent yields.