Stereoselective synthesis of α,β-unsaturated carboxylic acids from alkynes using the Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system

Reactive iron carbonyl species generated in situ using the Fe(CO)5/t-BuOK/CH3COOH/CH2Cl2 reagent system reacts with alkynes to give the corresponding α,β-unsaturated carboxylic acids after CuCl2·2H2O oxidation with some regio and stereoselectivity.

Reactive iron carbonyl species generated in situ using the Fe(CO)5/t-BuOK/CH3COOH/CH2Cl2 reagent system reacts with alkynes to give the corresponding α,β-unsaturated carboxylic acids after CuCl2·2H2O oxidation with some regio and stereoselectivity.Figure optionsDownload as PowerPoint slideHighlights
► Hydrocarboxylation of alkynes by using Fe(CO)5/t-BuOK/AcOH/CH2Cl2 reagent system.
► The Fe2(CO)9/t-BuOK/AcOH/CH2Cl2 reagent system is also useful for this conversion.
► Symmetrical alkynes undergo stereoselective hydrocarboxylation.
► Unsymmetrical alkynes undergo regio and stereoselective hydrocarboxylation.