Abstract
The regioselectivity of palladium-catalyzed arylation reactions of a series of nitrogen-containing vinyl ethers is reported. The presence of a β-amino substituent gives a profound influence on regiochemistry. Thus, the arylation of [2-(dimethylamino)ethoxy]ethene (1c) with a variety of aryl iodides and bromides provides the β-arylation products [2-[2-(dimethylamino)ethoxy]ethenyl]arenes (3) with at least 95% selectivity and in good yields. The corresponding arylation of butoxyethene is a nonselective process giving a mixture of α- and β-substitution products. The palladium-catalyzed arylation of 1c constitutes an entry to 2-arylethanals after cleavage of the enol ether. The directing effect of the amino group is discussed in terms of chelation with the intermediate arylpalladium halide
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