Tetrahedron

Direct transformation of dialkyl sulfates into alkyllithium reagents by a naphthalene-catalysed lithiation

D Guijarro, G Guillena, B Mancheño, M Yus

Index: Guijarro, David; Guillena, Gabricia; Mancheno, Balbino; Yus, Miguel Tetrahedron, 1994 , vol. 50, # 11 p. 3427 - 3436

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Citation Number: 33

Abstract

The lithiation of primary and secondary dialkyl sulfates with an excess of lithium powder in the presence of a catalytic amount of naphthalene (4 mol%) in THF at− 78° C leads to the corresponding alkyllithium reagents (1: 2 molar ratio) which react with different electrophiles, mainly carbonyl compounds, to yield after hydrolysis, the expected coupling products. This methodology represents an indirect way to transform alcohols into organolithium ...

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