Direct introduction of nitrogen and oxygen functionality with spatial control using copper catalysis.
- Author(s): Shaum, James B
- Fisher, David J
- Sroda, Miranda M
- Limon, Luis
- Read de Alaniz, Javier
- et al.
Published Web Locationhttps://doi.org/10.1039/c8sc03288b
Synthetic chemists have spent considerable effort optimizing the synthesis of nitrogen and oxygen containing compounds through a number of methods; however, direct introduction of N- and O-functionality remains challenging. Presented herein is a general method to allow for the simultaneous installation of N- and O-functionality to construct unexplored N-O heterocyclic and amino-alcohol scaffolds. This transformation uses earth abundant copper salts to facilitate the formation of a carbon-centered radical and subsequent carbon-nitrogen bond formation. The intermediate aminoxyl radical is terminated by an intramolecularly appended carbon-centered radical. We have exploited this methodology to also access amino-alcohols with a range of aliphatic and aromatic linkers.