Combined directed ortho metalation—intramolecular Friedel–Crafts connections. Regiospecific route to 1-substituted fluoren-9-ones

Combined directed ortho metalation—intramolecular Friedel–Crafts connections. Regiospecific route to 1-substituted fluoren-9-ones

ortho-Substituted-2-biphenyl carboxylic acids of the type 3a– j were prepared by the tandem metalation sequence from 2-biphenyl carboxylic acid 1 with sec-butyllithium in THF at −78°C followed by quenching with electrophiles. The carboxylic acids 3a– f were converted into 1-substituted fluorenones 4...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 43; no. 46; pp. 8347 - 8350
Main Authors: Tilly, David, Samanta, Subhendu S, Faigl, Ferenc, Mortier, Jacques
Format: Journal Article
Language:English
Published: Elsevier Ltd 11-11-2002
Online Access:Get full text
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Summary:ortho-Substituted-2-biphenyl carboxylic acids of the type 3a– j were prepared by the tandem metalation sequence from 2-biphenyl carboxylic acid 1 with sec-butyllithium in THF at −78°C followed by quenching with electrophiles. The carboxylic acids 3a– f were converted into 1-substituted fluorenones 4a– f upon treatment with methanesulfonic acid. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01976-7