Regioselective addition reactions of propargyl bromides to carbonyl compounds with gallium catalyzed by indium

Reactions of organogallium reagents generated from propargyl bromides having substituents at the gamma-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields. Treatment of organogallium reagents obtained from propargyl bromide or propargyl bromides having, substituents at the alpha-position and gallium in the presence of 5 mol % of indium with carbonyl compounds selectively afforded homopropargyl alcohols.