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Synthesis 2009(9): 1405-1427
DOI: 10.1055/s-0029-1216632
DOI: 10.1055/s-0029-1216632
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Transition-Metal-Catalyzed Site-Selective Cross-Coupling of Di- and Polyhalogenated Compounds
Weitere Informationen
Received
26 January 2009
Publikationsdatum:
14. April 2009 (online)
Publikationsverlauf
Publikationsdatum:
14. April 2009 (online)
Abstract
This review highlights transition-metal-catalyzed cross-coupling reactions in which one of the halogen atoms (or pseudo-halogen groups) of di- or polyhalogenated compounds is converted site-selectively into another group. The compounds are categorized as halogenated alkenes, heteroarene derivatives, benzene derivatives, and alkanes. Enantioselective cross-coupling of substrates having two enantiotopic halo groups is also described.
1 Introduction
2 Di- and Polyhalogenated Alkenes
2.1 1,1-Dihalogenated Alkenes
2.1.1 Grignard Reagents
2.1.2 Organozinc Reagents
2.1.3 Organostannanes and Others
2.1.4 Boronic Acids and Derivatives
2.1.5 Alkynes
2.2 1,2-Dihalogenated Alkenes
2.3 Trihalogenated Alkenes and Others
3 Di- and Polyhalogenated Heteroarene Derivatives
3.1 Five-Membered Heteroarene Derivatives
3.2 Six-Membered Heteroarene Derivatives
3.3 Other Heteroarene Derivatives
3.4 Mechanism
4 Di- and Polyhalogenated Benzene Derivatives
4.1 Polyhalogenated Benzenes
4.2 With Electron-Withdrawing Groups
4.3 With Electron-Donating Groups
4.4 Other Dihalogenated Benzenes
5 Dihalogenated Alkanes
6 Enantioselective Cross-Coupling Reactions
7 Conclusions
Key words
cross-coupling - catalysis - halides - transition metals - site selectivity
-
1a
Metal-Catalyzed Cross-Coupling Reactions
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