1-Bromo-3,5-dimethoxybenzene → 3-(3,5-Dimethoxyphenyl)-1-propene

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Reaction Steps

The Pd-catalyzed cross-coupling reaction of 5-Bromo-1,3-dimethoxybenzene with allyl boronic acid pinacol ester produced 5-allyl-1,3-dimethoxybenzene 1 in excellent yield. AlI3 will be used for demethylating 5-Allyl-1,3-dimethoxybenzene with CS2 as solvent to produce 5-allylresorcinol 2. The bis(phosphinite) PCP ligands 3 will be obtained by diphosphorylation of 5-allylresorcinol 2 with the respective chlorophosphine and sodium hydride as a base. Iridium complexes 4 will be obtained from reaction of the respective PCP ligands 3 with [Ir(COD)Cl]2 or [Ir(COE)2Cl]2. Hydrosilylation of complexes 4 will produce the hydrosilylated complexes 5. Reaction of complexes 5 with silica gel will afford the Si2O-supported Ir complexes 6. To date, 5-allyl-1,3-dimethoxybenzene 1 has been prepared in 92% yield.

Provenance & Evidence