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Issue 9, 2017
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Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions

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Abstract

An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and “filtered” over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A “one-pot” protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.

Graphical abstract: Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions

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Publication details

The article was received on 21 Feb 2017, accepted on 19 Apr 2017 and first published on 19 Apr 2017


Article type: Paper
DOI: 10.1039/C7GC00556C
Citation: Green Chem., 2017,19, 2286-2295
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    Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions

    M. Jereb and L. Hribernik, Green Chem., 2017, 19, 2286
    DOI: 10.1039/C7GC00556C

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