Functionalization of chlorobenzenes via their CpFe+ salts: a synthesis of substituted diphenyl ethers

Article abstract of DOI:10.1016/0022-328X(92)83357-N

In work directed towards the synthesis of functionalized diaryl ethers such as SK + F L-94901 the benzylic carbanion derived from 3-ethoxy-6-methylpyridazine-1-oxide was added ortho to an electron-withdrawing chloride group in (η⁵-cyclopentadienyl)(η⁶-1,4-dichlorobenzene)iron(1+) hexafluorophosphate(1-) and other η⁶-chloroarene cationic complexes to form neutral η⁵-cyclohexadienyl ligands.Oxidative aromatization of the adduct occurred with concomitant demetallation.In contrast to the Yanovsky-type reactions of the carbanion, chloride was displaced from (η⁶-1,4-dichlorobenzene)CpFe⁺ by phenoxide anions under mild conditions to give η⁶-diphenyl ether cationic complexes.