Preparation of ferrocenes with high fluorous-phase affinities

The reaction of 1,1′-bis(pentafluorophenyl)ferrocene with fluorous alkoxides having the general formula NaOCH2(CF2)nCF3 (n = 0, 2, 5, 7, and 8) afforded a series of ferrocenes of general formula {η5-4-[CF3(CF2)nCH2O]C6F4C5H4}2Fe (1). The reaction of 1,1′-bis(4-tetrafluoropyridyl)ferrocene with the same fluorous alkoxides afforded a series of ferrocenes of general formula (η5-4-{2,6-[CF3(CF2)nCH2O]2C5F2N}C5H4)2Fe (2). Perfluoro(methylcyclohexane)/toluene partition coefficients increase with the number (2 or 4) and length (n) of the fluorous substituent. Complexes 1a and 2a (both n = 0) were structurally characterized.