Arene-catalysed lithiation reactions with lithium at low temperature

The reaction of functionalized alkyl chlorides or phenyl sulphides with an excess of lithium powder in the presence of a catalytic amount of an arene (1%; naphthalene, biphenyl, 4,4′-di-tert-butylbiphenyl) in tetrahydrofuran (THF) at –78 °C gives the corresponding organolithium compounds, which react with electrophiles such as water, iso-butyraldehyde, or cyclohexanone to yield the expected reaction products.