Transition-Metal-Catalyzed Site-Selective Cross-Coupling of Di- and Polyhalogenated Compounds

This review highlights transition-metal-catalyzed cross-couplingreactions in which one of the halogen atoms (or pseudo-halogen groups)of di- or polyhalogenated compounds is converted site-selectivelyinto another group. The compounds are categorized as halogenatedalkenes, heteroarene derivatives, benzene derivatives, and alkanes.Enantioselective cross-coupling of substrates having two enantiotopichalo 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