Tetrahedron

Naphthalene-catalysed lithiation of allylic and benzylic mesylates: a new method for allyl, methallyl, and benzyl lithium

D Guijarro, B Mancheño, M Yus

Index: Guijarro, D.; Mancheno, B.; Yus, M. Tetrahedron, 1992 , vol. 48, # 22 p. 4593 - 4600

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Citation Number: 62

Abstract

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° 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° C by adding the corresponding mesylate together with the electrophile to a suspension of ...