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

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 a...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-11, Vol.137 (46), p.14590-14593
Main Authors: Howell, Jennifer M, Feng, Kaibo, Clark, Joseph R, Trzepkowski, Louis J, White, M. Christina
Format: Article
Language:English
Subjects:
Carbon - chemistry
Hydrogen - chemistry
Nitrogen - chemistry
Oxidation-Reduction
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b10299