Issue 46, 2018

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.

Graphical abstract: Direct introduction of nitrogen and oxygen functionality with spatial control using copper catalysis

Supplementary files

Article information

Article type
Edge Article
Submitted
25 jul 2018
Accepted
17 sep 2018
First published
17 sep 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 8748-8752

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

J. B. Shaum, D. J. Fisher, M. M. Sroda, L. Limon and J. Read de Alaniz, Chem. Sci., 2018, 9, 8748 DOI: 10.1039/C8SC03288B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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