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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

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

Shaum James B JB Fisher David J DJ Sroda Miranda M MM Limon Luis L Read de Alaniz Javier J

Chemical science 20180917 46

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-centere ...[more]

PMID: 30627395

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