The Heck reaction of polymer-supported allylamine with aryl iodides

The Heck reaction of Wang resin-bound allylamine with aryl iodides produces various, substituted cinnamylamines. The catalyst and additive system consisting of palladium(II) acetate, n-Bu4NOAc and potassium chloride, in addition to potassium carbonate in N,N-dimethylformamide, accomplishes a regioselective γ-arylation. By utilising the easily formed and stable carbamate linker on Wang resin, the incompatibility of free amines with the palladium catalyst is avoided. The cinnamylamine products are cleaved from the resin with trifluoroacetic acid under mild conditions and are converted into chromatographically separable acetamides. Our solid-phase method offers a new alternative for the synthesis of cinnamylamine derivatives, as biologically interesting compounds and useful synthetic intermediates.