Initiated by Heck isomerization of aryl bromides and allyl alcohols, the intermediate 3-arylpropanal is readily transformed into 3-arylmethylindoles by Fischer indole synthesis in a consecutive three-component fashion in moderate to good yields. This Heck isomerization–Fischer indolization (HIFI) sequence can be readily concatenated into a four-component Heck isomerization–Fischer indolization–alkylation (HIFIA) synthesis affording products in good to excellent yields.