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

Cedrick Veryser, Joachim Demaerel, Vidmantas Bieliu̅nas, Philippe Gilles and Wim M. De Borggraeve*

*Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Box 2404, 3001 Leuven, Belgium, Email: wim.deborggraevekuleuven.be

C. Veryser, J. Demaerel, V. Bieliu̅nas, P. Gilles, W. M. De Borggraeve, Org. Lett., 2017, 19, 5244-5247.

DOI: 10.1021/acs.orglett.7b02522 (free Supporting Information)


Abstract

Rapid ex situ generation of gaseous sulfuryl fluoride (SO2F2) from 1,1′-sulfonyldiimidazole as a precursor enables a convenient transformation of phenols into the corresponding aryl fluorosulfates using a two-chamber reactor. Various phenols and hydroxylated heteroarenes were fluorosulfated in good to excellent yields.

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Key Words

fluorosulfates


ID: J54-Y2017