Position-Flexible Elaboration of Halogenated Heterocycles: Metalated Species as Key Intermediates for Synthesis

Manfred Schlosser

doi:10.1055/s-2007-992384

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Synlett 2007(20): 3096-3102
DOI: 10.1055/s-2007-992384

ACCOUNT

Position-Flexible Elaboration of Halogenated Heterocycles: Metalated Species as Key Intermediates for Synthesis

Manfred Schlosser*
Institute of Chemical Sciences and Engineering (ISIC), Ecole Polytechnique Fédérale, BCh, 1015 Lausanne, Switzerland
Fax: +41(21)6939365; e-Mail: manfred.schlosser@epfl.ch;

Further Information

Publication History

Received 18 September 2007
Publication Date:
03 December 2007 (online)

Abstract
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Abstract

Halogens, in particular fluorine atoms, are favorite tools to fine-tune the chemical and biological properties of pharmaceutical or agricultural development products. At the same time, such an electronegative substituent can effectively assist the site-selective functionalization of an aromatic or heterocyclic core compound by directing a metal to the targeted position, the metal acting as a harbinger for the definitive substituent. The concept is illustrated by typical examples selected from the carbazole, indole, pyrrole, pyrazole, imidazole, pyridine, quinoline and pyrimidine fields.

1 Introduction

2 Carbazoles and Indoles

3 Pyrroles, Pyrazoles and Imidazoles

4 Pyridines, Quinolines and Pyrimidines

5 Conclusions and Outlook

Key Words

fluorine - functionalization - halogens - organometallic reagents - organic synthesis - regioselectivity

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Leroux, F.; Ginanneschi, A.; Schlosser, M. unpublished results, 2005.