Copper-Mediated Selective Cross-Coupling of 1,1-Dibromo-1-alkenes and Heteronucleophiles: Development of General Routes to Heterosubstituted Alkynes and Alkenes

Efficient and general procedures for the cross coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site selective, double, or alkynylative cross coupling, therefore providing divergent and straightforward entries to numerous building blocks such as bromoenamides, ynamides, ketene N,N-acetals, bromoenol ethers ynol ethers, ketene O,O-acetals, or vinylphosphonates and further expanding the copper catalysis toolbox with useful and versatile processes.