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Synthesis 2009(9): 1405-1427  
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

Jia-Rui Wang, Kei Manabe*
Manabe Initiative Research Unit, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako 351-0198, Japan
Fax: +81(48)4624662; e-Mail: keimanabe@riken.jp;
Further Information

Publication History

Received 26 January 2009
Publication Date:
14 April 2009 (online)

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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