Processing Aryllithium and Hetaryllithium Intermediates: Formation of Halogen and Chalcogen Derivatives

D. W. Slocum; Phillip Shelton; Kelley M. Moran

doi:10.1055/s-2005-918495

REVIEW

Processing Aryllithium and Hetaryllithium Intermediates: Formation of Halogen and Chalcogen Derivatives

D. W. Slocum*, Phillip Shelton, Kelley M. Moran
Department of Chemistry, Western Kentucky University, 1906 College Heights Blvd, Bowling Green, KY 42101-1079, USA
Fax: +1(270)7455361; e-Mail: Donald.Slocum@wku.edu;

Abstract

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Abstract

Introduction of a halogen (F, Cl, Br, I) or a chalcogen (O, S, Se, Te) via the intermediacy of an aryllithium or hetaryllithium is reviewed. Representative examples are presented to demonstrate the range of substituted aromatic compounds accessible via formation of the lithio-intermediate followed by treatment with an appropriate derivatizing agent. Where possible, the merits and the limitations of the various reagents utilized for introduction of a specific halogen or chalcogen are discussed.

1 Background
2 Halogenation
2.1 Fluorination
2.2 Chlorination
2.3 Bromination
2.4 Iodination
2.5 Conclusions Regarding Halogenations
3 Chalcogenation
3.1 Hydroxylation
3.2 Introduction of Sulfur
3.3 Introduction of Selenium
3.4 Introduction of Tellurium
3.5 Conclusions Regarding Chalcogenations
4 General Conclusions

Key words

aromatic - chalcogens - halogens - lithiations - metalations

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