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Manganese‐Dioxide‐Catalyzed Trifluoromethylation and Azidation of Styrenyl Olefins via Radical Intermediates

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Manganese dioxide catalyzed trifluoromethylation of styrenes and enolacetates using Langlois reagent is reported. Employing oxygen/air as the oxidant, styrenes afforded a mixture of the trifluoromethylacohol and ketone products in good… Click to show full abstract

Manganese dioxide catalyzed trifluoromethylation of styrenes and enolacetates using Langlois reagent is reported. Employing oxygen/air as the oxidant, styrenes afforded a mixture of the trifluoromethylacohol and ketone products in good overall yield. The protocol also works successfully for converting α-methylstyrene precursors to the corresponding trifluoromethyl alcohols. The keto-trifluoromethylated products could be obtained exclusively upon employing enolacetates as substrates under the same reaction conditions. The method was extended to the radical azidation of enolacetates using azidotrimethylsilane to furnish the corresponding azido-ketones in good yields.

Keywords: trifluoromethylation azidation; dioxide catalyzed; catalyzed trifluoromethylation; manganese dioxide

Journal Title: Asian Journal of Organic Chemistry
Year Published: 2018

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