Arylmethyl thioethers

Ethyl format el aryl magnesium bromide Arylmethyl thioethers s. 18, 664... 

Arylmethyl(homobenzyl)ethylsulfonium salts are appropriate substrates for Suzuki-type coupling reactions. In this reaction, performed on a polymer-bound sulfonium tetrafluoroborate, the benzyl fragment on the sulfur atom was transferred to the boronic acid residue. The sulfonium salt was prepared from an al-kylthiol resin by alkylation with a substituted benzyl halide to give thioether 98 and subsequent alkylation with triethyloxonium tetrafluoroborate. Reaction with a boronic acid derivative yielded diaryl methanes 99 [94] (Scheme 6.1.22). 

The following discussion will be focused on the effect of structural variations on the kinetics of fragmentation, the cleavage mode, and the stepwise or concerted nature of the process. Similar concepts have also been applied to the reductive cleavage reactions of other series of substrates, i.e. a-substituted acetophenones [246-250], perbenzoates [240, 251], peroxides [242, 252-256], sulfides [244, 257, 258], sulfonium salts [259-263], nitrocumenes [264, 265], arylmethyl aryl ethers and thioethers [266-270]. 

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