Direct Transformation of Allylic and Benzylic Alcohols or Their Silylated Derivatives into Orgnolithium Compounds

Article abstract of DOI:10.1016/0040-4020(95)00709-H

The reaction of allylic or benzylic alcohols 1 with n-butyllithium followed by treatment with lithium powder and a catalytic amount of DTBB (5 mol percent) in THF at room temperature gives a solution of the corresponding alkyllithium reagent, which reacts in situ with different electrophiles to yield the expected products 2.Alternatively, the O-silylated derivatives of the same alcohols are lithiated under Barbier-type reaction conditions to afford the same reaction products with better yields.