Direct introduction of nitrogen and oxygen functionality with spatial control using copper catalysis.

ABSTRACT: 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.

SUBMITTER: Shaum JB 

PROVIDER: S-EPMC6289103 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature