3-(Hetero)aryl propenals or propenones are efficiently prepared by a Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using Beller′s CataCXium® Ptb ligand under Jeffery′s and Fu′s conditions. The formation of [a] Scheme 3. Consecutive three-component Heck-cyclocondensation synthesis of 3(,5)-substituted pyrazoles 4.

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.

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Initiated by Heck isomerization of aryl bromides and allyl alcohols, the intermediate 3-arylpropanal is readily transformed into 3arylmethylindoles by Fischer indole synthesis in a consecutive threecomponent 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.

starting from simple materials such as (hetero)aryl bromides, allyl alcohols, hydrazines, and alkyl bromides