Work

Selective Heteroaryl N-Oxidation of Amine-Containing Molecules

Year: 2018

Type: article

Abstract: The first examples of nonenzymatic N-oxidation of heteroarenes in the presence of amines are reported. Pyridine, quinoline, and isoquinoline N-oxides are selectively formed in the presence of more reactive aliphatic and alicyclic amines by use of an in situ protonation strategy and an iminium salt organocatalyst. Application to late-stage functionalization that mimics phase 1 metabolism of small-molecule drugs is also demonstrated.

Source: Organic Letters

DOI: 10.1021/acs.orglett.8b00558

Authors: Robert M. B. Dyer, Philip L. Hahn, Michael K. Hilinski

Institution: University of Virginia

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: University of Virginia, American Chemical Society Petroleum Research Fund, National Institute of General Medical Sciences

Awards: Organocatalytic Site-Selective C-H Bond Functionalization, G8773995450