Solvent and ligand effects on selective mono- and dilithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles

K. Fogassy, K. Kovács, G. M. Keseru, L. Toke, F. Faigl

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Abstract

Novel methods for site-selective lithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles are described. Mono- or dilithiations are governed by change of both the temperature and the solvent from tetrahydrofuran to diethyl ether. Regioselectivities could be influenced by the quality of the metallating agent. Thus, 1-(4-chlorophenyl)pyrrole was dilithiated with activated butyllithium at 0 °C to afford a valuable intermediate in a pyrrolobenzoxazepine synthesis.

Original languageEnglish
Pages (from-to)1039-1043
Number of pages5
JournalJournal of the Chemical Society. Perkin Transactions 1
Issue number9
DOIs
Publication statusPublished - Jan 1 2001

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ASJC Scopus subject areas

  • Chemistry(all)

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