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Synthesis 2005(20): 3477-3498
DOI: 10.1055/s-2005-918495
DOI: 10.1055/s-2005-918495
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Processing Aryllithium and Hetaryllithium Intermediates: Formation of Halogen and Chalcogen Derivatives
Weitere Informationen
Received
27 June 2005
Publikationsdatum:
24. November 2005 (online)
Publikationsverlauf
Publikationsdatum:
24. November 2005 (online)
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.
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1 Background
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2 Halogenation
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2.1 Fluorination
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2.2 Chlorination
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2.3 Bromination
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2.4 Iodination
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2.5 Conclusions Regarding Halogenations
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3 Chalcogenation
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3.1 Hydroxylation
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3.2 Introduction of Sulfur
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3.3 Introduction of Selenium
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3.4 Introduction of Tellurium
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3.5 Conclusions Regarding Chalcogenations
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4 General Conclusions
Key words
aromatic - chalcogens - halogens - lithiations - metalations
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