NAPHTHALENE-CATALYZED LITHIATION OF ALLYLIC AND BENZYLIC MESYLATES - A NEW METHOD FOR ALLYL, METHALLYL, AND BENZYL LITHIUM

The reaction of allylic or benzylic mesylates (1) with an excess of lithium powder and a catalytic amount of naphthalene (4 mol %) in THF at -78-degrees-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-degrees-C by adding the corresponding mesylate together with the electrophile to a suspension of the activated lithium in THF, in a Barbier-type reaction.