Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water

Abstract

A simple and efficient method for synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is presented.

Selenomethoxylation of Alkenes Promoted by Oxone®

“…Regarding its use in the synthesis of organochalcogen compounds, Oxone® was used in the oxidation of sulfides to sulfoxides and sulfones, oxidation of thiols to sulfonic acids, oxyhalogenation of thiols and disulfides, oxidative coupling of thiols to disulfides, oxidation of selenides to selenones, and in the enantioselective oxidation of disulfides . Oxone® was used to prepare symmetric thiosulfonates, 3‐arylthio indoles, and 2‐aminobenzothiazoles …”

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

“…A potential reaction cycle, proposed in Scheme 7 is similar to the one proposed by Madabhushi. 38 Ammonium nitrate decomposition in the acidic medium yielded NO/NO 2 , which are the key players in the catalytic cycle. Indeed, during the experiments it was possible to observe several consecutive appearances and disappearances of brown gas.…”

“…NCS/Bu 4 NCl, 24 TCCA/BnMe 3 NCl, [25][26][27] chloramine-T/Bu 4 NCl, 28 DCH/BnMe 3 NCl, 29 33 NaOCl/HCl, 34 PCBS or TCBDA/BnMe 3 NCl, 35 nitrate salt with TMSCl 36 or sulfuryl chloride, 37 and oxone/KX. 38 In addition, the sole oxidants may play a dual role also as a source of chloride i.e. NaOCl·5H 2 O, 39 NCS, 40 DCDMH, 41 and ClO 2.…”

Regioselective Halogenation of 2H‐Chromenones Promoted by Oxone and NaX: A Facile Approach for the Preparation of Halochromenones and 2H‐Chromenone Natural Products

“…The oxidative halogenation of α,β‐enones/alkenes, arenes, amides/lactams/carbamates, aromatic methyl ketones, allylic/homoallylic alcohols, thiols/disulfides, and pyrazoles have been reported with the combination of oxone and metal halides (NaX/KX). There is another report by using HBr in presence of oxone in DCM solvent .…”