ARENE-CATALYZED 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-degrees-C gives the corresponding organolithium compounds, which react with electrophiles such as water, iso-butyraldehyde, or cyclohexanone to yield the expected reaction products.