Over the past years, we have shown that chlorotrimethylsilane-nitrate salt system acts as very efficient reagent for Friedel-Crafts nitration of aromatics, ipso-nitration of aryl boronic acids, oxychlorination of thiols and disulfides and oxidation of sulfides to sulfones. Chloro/bromotrimethylsilane-nitrate salt reagent system can also carry out halogenation of acetophenones. In our recent studies with the system, we found that β-chloro and bromostyrenes can be prepared from the corresponding cinnamic acid derivatives by halodecarboxylation with high efficacy under suitable conditions. Mechanistic aspects and extension of the study towards the synthesis of other β-substituted derivatives will also be discussed.

Regioselective synthesis of chloro/bromostyrenes: Chloro/bromotrimethylsilane-nitrate salt as efficient reagent system

249th National Meeting (2015)

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