A novel consecutive three-component four step synthesis of 5-(hetero)arylpent-2-enoates has been disclosed. Various (hetero)aryl iodides can be coupled with allyl alcohol under Heck conditions to give 3-(hetero)arylpropionaldehyde intermediates, which were transformed without isolation with in situ generated stabilized phosphorus ylides to furnish 5-(hetero)arylpent-2-enoates in moderate to excellent yield. This one-pot procedure circumvents the isolation of sensitive aldehydes and phosphorus ylides as intermediates and finally gives the product isomers with good to excellent E/Z and β/α selectivity.