Tetrahedron p. 4593 - 4600 (1992)
Update date:2022-08-06
Topics: Naphthalene Lithiation Allylic Benzylic Catalysed Allyl Benzyl Mesylates
Guijarro, D.
Mancheno, B.
Yus, M.
The reaction of allylic or benzylic mesylates (1) with an excess of lithium powder and a catalytic amount of naphthalene (4 mol percent) in THF at -78 deg 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 deg C by adding the corresponding mesylate together with the electrophile to a suspension of the activated lithium in THF, in a Barbier-type reaction.
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