[[abstract]]Palladium-catalyzed reaction of aryl bromides with 7-hydroxy-1,3-dienes proceeded in different reaction paths depending on the structure of the starting substrates. With cyclic 7-hydroxy-1,3-dienes, the reaction proceeded in the 1,4-alkoxyarylation fashion. While with acyclic 7-hydroxy-1,3-dienes, the reaction produced 1,2-alkoxyarylation products. Palladium(0) catalyzed intramolecular cyclization of cyclohexa-1,3-diene bearing a diketo functionality at C-5 yielded bicyclo[4.1.0]heptene derivative with the vinyl group at the C-1 position of the ring. Platinum(II) chloride catalyzed intramolecular cyclization of cyclohexa-1,3-diene bearing a terminal alkynyl side chain in alcoholic solvent afforded bicyclo[4.3.0]nonene derivative with an alkoxy group at C-4 position of the bicyclic ring. Gold(I) intramolecular cyclization of cyclohexa-1,3-diene bearing a terminal phenyl alkyne produce tetracyclic compounds. While an electron-withdrawing group present at the phenyl, cyclization produced fused bicyclic skeletons.
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