Issue 9, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Katalin Fogassy,a   Krisztina Kovács,a   György M. Keserű,b   László Tőkea  and  Ferenc Faigl*a  

* Corresponding authors

a Department of Organic Chemical Technology, Budapest University of Technology and Economics, Budapest, Hungary

b Department of Chemical Informatical Technology, Budapest University of Technology and Economics, Budapest, Hungary

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.

Graphical abstract: Solvent and ligand effects on selective mono- and dilithiation of 1-(chlorophenyl)pyrroles and 1-(methoxyphenyl)pyrroles [ ]

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B100008J
Article type
Paper
Submitted
02 Jan 2001
Accepted
22 Mar 2001
First published
18 Apr 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1039-1043

Permissions

Request permissions

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

K. Fogassy, K. Kovács, G. M. Keserű, L. Tőke and F. Faigl, J. Chem. Soc., Perkin Trans. 1, 2001, 1039 DOI: 10.1039/B100008J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements