Copper-Catalyzed Propargylation of Nitroalkanes

Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient alpha-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these alpha-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered Nheterocycles such as pyrroles and 2-pyrrolines.