Remote functionalisation via sodium alkylamidozincate intermediates: access to unusual fluorenone and pyridyl ketone reactivity patterns

Abstract

Treating fluorenone or 2-benzoylpyridine with the sodium zincate [(TMEDA)·Na(μ-^tBu)(μ-TMP)Zn(^tBu)] in hexane solution, gives efficient ^tBu addition across the respective organic substrate in a highly unusual 1,6-fashion, producing isolable organometallic intermediates which can be quenched and aerobically oxidised to give 3-tert-butyl-9H-fluoren-9-one and 2-benzoyl-5-tert-butylpyridine respectively.