No abstract

1,2-Dihaloalkenes readily undergo simultaneous or sequential difunctionalization through transition-metal-catalyzed reactions, which makes them attractive building blocks for complex unsaturated motifs. This review summarizes recent applications of such transformations in C–C and C–heteroatom bond forming processes. The facile synthesis of stereodefined alkene derivatives, as well as aromatic and heteroatomic­ compounds, from 1,2-dihaloalkenes is thus outlined.1 Introduction2 Synthesis of 1,2-Dihaloalkenes3 C–C Bond Forming Reactions4 C–Heteroatom Bond Forming Reactions5 Conclusion

: The first intermolecular examples of copper-catalyzed cross-coupling between (E)-1,2-diiodoethene and various carbazates are reported here. (E)-β-iodovinylcarbazates were prepared with a complete retention of the olefin configuration. Favored regioisomer depends on the substrate’s structure. Subsequent functionalization of a model (E)-N-(β-iodovinyl)carbazate via cross-coupling reactions led to a variety of β-functionalized (E)-N-alkenylcarbazates with up to very good yields.