Abstract
The Heck arylation of acrolein with a variety of condensed aryl and heteroaryl halides is described. Depending on the substrate, up to 87% isolated yield to the expected aldehydes was achieved. When the reaction was run on diethylacetal acrolein, the choice of catalytic system dramatically affected the selectivity of the reaction: the catalyst system based on Herrmann’s palladacycle complex gave mainly saturated esters 2, whereas Cacchi’s conditions led to the formation of α,β-unsaturated aldehydes 1.
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