Selective Heteroaryl N-Oxidation of Amine-Containing Molecules,Organic Letters

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Selective Heteroaryl N-Oxidation of Amine-Containing Molecules
Organic Letters ( IF 4.9 ) Pub Date : 2018-03-16 00:00:00 , DOI: 10.1021/acs.orglett.8b00558
Robert M. B. Dyer ₁ , Philip L. Hahn ₁ , Michael K. Hilinski ₁

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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.

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