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

Cedrick Veryser | Zendy; Joachim Demaerel | Zendy; Vidmantas Bieliūnas | Zendy; Philippe Gilles | Zendy; Wim M. De Borggraeve | Zendy

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

Author(s) -

Cedrick Veryser,

Joachim Demaerel,

Vidmantas Bieliūnas,

Philippe Gilles,

Wim M. De Borggraeve

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b02522

Subject(s) - chemistry , aryl , in situ , fluoride , combinatorial chemistry , stereochemistry , organic chemistry , inorganic chemistry , alkyl

A convenient transformation of phenols into the corresponding aryl fluorosulfates is presented: the first protocol to completely circumvent direct handling of gaseous sulfuryl fluoride (SO 2 F 2 ). The proposed method employs 1,1'-sulfonyldiimidazole as a precursor to generate near-stoichiometric amounts of SO 2 F 2 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.

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