Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates

Veryser, Cedrick; Demaerel, Joachim; Bieliunas, Vidmantas; Gilles, Philippe; De Borggraeve, Wim M

doi:10.1021/acs.orglett.7b02522

Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates

Author:

Veryser, Cedrick

Demaerel, Joachim ; Bieliunas, Vidmantas ; Gilles, Philippe ; De Borggraeve, Wim M

Keywords:

Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, COUPLING REACTIONS, PALLADIUM, SUFEX, CHEMISTRY, PHENOLS, ACIDS, TRIETHYLAMINE, POLYSULFATES, REPLACEMENT, SO2F2, COSMIC - 721290;info:eu-repo/grantAgreement/EC/H2020/721290, 03 Chemical Sciences, Organic Chemistry, 34 Chemical sciences

Abstract:

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.