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

Authors
Fogassy, K Kovacs, K Keseru, GM Toke, L Faigl, F
Citation
K. Fogassy et al., Solvent and ligand effects on selective mono- and dilithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles, J CHEM S P1, (9), 2001, pp. 1039-1043
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
9
Year of publication
2001
Pages
1039 - 1043
Database
ISI
SICI code
1472-7781(2001):9<1039:SALEOS>2.0.ZU;2-6
Abstract
Novel methods for site-selective lithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles are described. Mono- or dilithiations are govern ed by change of both the temperature and the solvent from tetrahydrofuran t o diethyl ether. Regioselectivities could be influenced by the quality of t he metallating agent. Thus, 1-(4-chlorophenyl)pyrrole was dilithiated with activated butyllithium at 0 degreesC to afford a valuable intermediate in a pyrrolobenzoxazepine synthesis.