The alkoxycarbonylation of protected propargyl alcohols

Palladium-catalyzed alkoxycarbonylation of the C≡C triple bond of propargyl alcohol is a sustainable synthetic approach to 2-(hydroxymethyl)acrylates, a family of valuable intermediates. The developed synthetic protocol includes protection of the alcoholic function of the alkyne before its carbonylation in the presence of Drent’s catalytic system. Protection step effectively extends the catalyst life hence enhancing the practical applicability of the reaction. The effectiveness of some different protecting groups (benzyl, acetyl and trimethylsilyl) has been assessed and the influence of the reaction parameters investigated.Palladium-catalyzed alkoxycarbonylation of the C≡C triple bond of propargyl alcohol is a sustainable synthetic approach to 2-(hydroxymethyl)acrylates, a family of valuable intermediates. The developed synthetic protocol includes protection of the alcoholic function of the alkyne before its carbonylation in the presence of Drent's catalytic system. Protection step effectively extends the catalyst life hence enhancing the practical applicability of the reaction. The effectiveness of some different protecting groups (benzyl, acetyl and trimethylsilyl) has been assessed and the influence of the reaction parameters investigated