C,O-dilithiated diarylmethanols: Easy and improved preparation by naphthalene-catalysed lithiation of diaryl ketones and reactivity toward electrophiles

Article abstract of DOI:10.1016/S0040-4020(01)85822-1

The lithiation of different diaryl ketones 1 with an excess of lithium powder and a catalytic amount (8 mol %) of naphthalene in tetradrofuran at -30°C leads to the formation of the corresponding dianions of the type I, with Met=Li, which react with several electrophiles (E⁺=MeI, EtBr, Pr(i)CHO, PhCHO, cyclohexanone, MeCN) to give, after hydrolysis, the expected substituted diarylmethanols 2.