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Remote Oxidation of Aliphatic C–H Bonds in Nitrogen-Containing Molecules

2015; American Chemical Society; Volume: 137; Issue: 46 Linguagem: Inglês

10.1021/jacs.5b10299

1943-2984

Jennifer L. Howell, Kaibo Feng, Joseph R. Clark, Louis J. Trzepkowski, M. Christina White,

Synthesis and Catalytic Reactions

Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Brønsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)–H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.