Alkylation of Magnesium Sulfinates:  A Direct Transformation of Functionalized Aromatic/Heteroaromatic Halides into Sulfones

Abstract

[reaction: see text] Sulfinate alkylation is one of the conventional methods for sulfone synthesis. The alkylation of magnesium sulfinates, which are easily accessible via reactions of organomagnesium intermediates with sulfur dioxide, provides a convenient route for sulfone preparation. In this communication, we report a preliminary study of the alkylation of arylmagnesium sulfinates. An application of this reaction to directly transform functionalized aromatic/heteroaromatic halides into sulfones is also described.

Profiling thiol metabolites and quantification of cellular glutathione using FT-ICR-MS spectrometry

“…Whereas hypotaurine (Fig. 5), a sulfinic acid intermediate of taurine biosynthesis [48], is not a thiol, it reacts similarly due to the nucleophilicity of the sulfinic sulfur atom [49]. The assignments of hypotaurine and homocysteine (entries 4 and 5) were confirmed using CID MS/MS analysis, see Electronic Supplementary Material Figs.…”

Preparation of Disubstituted Phenyl Propargyl Alcohols, their Use in Oxathiolene Oxide Synthesis, and Evaluation of the Oxathiolene Oxide Products as Anticarcinogenic Enzyme Inducers

“…Instead, we presume that 33 and 34 are formed from reactions of organomagnesium species with SO 2 [35] and that these 2 intermediates react to form 35 which is hydrolyzed to 30 (Scheme 5). …”

The Development and Application of Sulfur Dioxide Surrogates in Synthetic Organic Chemistry

“…[59][60][61][62] This reaction is particularly attractive as these salts are versatile starting materials for a wide range of sulfonyl-containing functional groups, such as sulfonyl chlorides, [62] sulfonamides, [59] and sulfones. [60,63,64] However, the commercial availability of metal sulfinates is limited to a handful of sodium salts and so the ability to generate them from readily available and easily accessible organometallic reagents expands the scope of the method greatly. Despite this, it is the requirement to use sulfur dioxide gas which has limited the uptake of this reaction, with oxidative routes to these important functional groups often being preferred.…”