Competition and co-operation between ortho directing groups and activating agents: Regioselective metallation of 1-(methoxyphenyl)pyrroles

✍ Scribed by Ferenc Faigl; Katalin Fogassy; Angelika Thurner; László Tőke

• Book ID: 104207705
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 309 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00183-x

✦ Synopsis

The role of di-and tri-dentate tertiary amine type ligands was studied in regioselective lithiation reactions of l-(methoxyphenyl)pyrroles with butyllithium (LIC). Clean ~-metallation of tile pyrrole ring oceured when N,N,N',N',N"-pentamethyldiethylenetriamine (PMDTA) was used while the benzene ring was lithiated ortho position to the methoxy group in the presence of N,N,N',N'tetramethylethylenediamine (TMEDA).