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

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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

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Publication details

The article was received on 25 Jul 2018, accepted on 17 Sep 2018 and first published on 17 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC03288B
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    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, Advance Article , DOI: 10.1039/C8SC03288B

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