Naphthalene-catalysed lithiation of 2-(chlorophenyl)-1,3-dioxolanes: Generation of formyl- and acetyl-phenyllithium equivalents [1]
1999; Elsevier BV; Volume: 55; Issue: 13 Linguagem: Inglês
10.1016/s0040-4020(99)00092-7
ISSN1464-5416
AutoresFernando F. Huerta, Cecilia Gómez, Miguel Yus,
Tópico(s)Chemical Reaction Mechanisms
ResumoThe reaction of 2-(chlorophenyl)-1,3-dioxolanes 1 with an excess of lithium powder and a catalytic amount of naphthalene (5 mol %) in the presence of different carbonyl compounds [tBuCHO, Et2CO, (CH2)5CO, PhCOMe] as electrophiles (Barbier-type conditions) in THF at −78°C leads, after hydrolysis with water at the same temperature, to the expected products 3, the corresponding intermediates involved being formyl- or acetyl-phenyl anion equivalents.
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