Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates
journal contributionposted on 2017-09-13, 14:36 authored by Cedrick Veryser, Joachim Demaerel, Vidmantas Bieliu̅nas, Philippe Gilles, Wim M. De Borggraeve
A 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.