Divergent C-H Oxidative Radical Functionalization of Olefins to Install Tertiary Alkyl Motifs Enabled by Copper Catalysis

An efficient tertiary alkylation reaction of olefins with 1,3-dicarbonyl compounds was developed by virtue of copper catalyst without the use of expensive ligands or additives. In contrast to alkyl Heck-type reaction, alkyl halide is not required. Notably, by varying the nitrogen and air atmosphere, the reaction selectively produces alkylation and alkylation oxygenation products, respectively. Initial investigations revealed that an alpha-carbonyl alkyl radical species might be involved in the process.