Naphthalene-Catalysed Lithiation of Allylic and Benzylic Mesylates: A New Method for Allyl, Methallyl, and Benzyl Lithium

Article abstract of DOI:10.1016/S0040-4020(01)81233-3

The reaction of allylic or benzylic mesylates (1) with an excess of lithium powder and a catalytic amount of naphthalene (4 mol percent) in THF at -78 deg C leads to a solution of the corresponding organolithium derivatives, which by treatment with different electrophiles yield the expected products 2-7.As an alternative route, the process can be carried out at 0 deg C by adding the corresponding mesylate together with the electrophile to a suspension of the activated lithium in THF, in a Barbier-type reaction.