Synthesis 2003(2): 0233-0242
DOI: 10.1055/s-2003-36828
PAPER
© Georg Thieme Verlag Stuttgart · New York

Expeditious Functionalization of Quinolines in Positions 2 and 8 via Polyfunctional­ Aryl- and Heteroarylmagnesium Intermediates

Anne Staubitz, Wolfgang Dohle, Paul Knochel*
Department für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 München, Germany
e-Mail: Paul.Knochel@cup.uni-muenchen.de;
Further Information

Publication History

Received 14 November 2002
Publication Date:
22 January 2003 (online)

Abstract

An efficient way to prepare functionalized 8-iodo-2-trifluoromethanesulfonyloxyquinolines is presented. The iodo functionality could be selectively converted into other residues via an iodine-magnesium exchange reaction. In addition, the trifluoromethanesulfonate functionality was used as a leaving group in Negishi cross-coupling reactions.