Direct introduction of nitrogen and oxygen functionality with spatial control using copper catalysis. Issue 46 (26th September 2018)

• Record Type: Journal Article
• Authors: Shaum, James B.; Fisher, David J.; Sroda, Miranda M.; Limon, Luis; Read de Alaniz, Javier
• Is Part Of: Chemical science. Volume 9:Issue 46(2018)
• Page Start: 8748
• Page End: 8752
• Publication Date: 2018-09-26
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8sc03288b
• Languages: English
• ISSNs: 2041-6520

Abstract

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. 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.