Conversion of aromatic ketones, benzyl alcohols, and alkyl aryl ethers to aromatic hydrocarbons with lithium 4,4'-di-t-butylbiphenyl radical anion

Article abstract of DOI:10.1016/S0040-4039(00)97012-6

Treatment of tetrahydrofuran (THF) solutions of the title compounds with excess lithium (or potassium) metal under ultrasonic irradiation in the presence of catalytic amounts of the electron-transfer agent 4,4'-di-t-butylbiphenyl (DBB) caused conversions to aromatic hydrocarbons in good yields. Addition of 1 or 2 equiv of alkyl halides prior to aq ammonium chloride treatment during workup provided mono- or di-alkylated products.