Abstract
The direct lithiation of simple alkoxyphenols has been studied both from a theoretical and an experimental viewpoint. Efficient lithiations were achieved by using a 2:1 tBuLi-tBuOLi mixture (LICLIOR) in THF at room temperature. In most cases alkoxy groups are responsible for the regioselectivity observed, although for the case of 2-methoxyphenol both the OMe and OLi groups actually act as ortho-directing groups during lithiation. Demethylation has been shown to be a common side reaction of lithiation of phenolic or nonphenolic alkoxy aromatics
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