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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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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
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Language:English
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cited_by cdi_FETCH-LOGICAL-a483t-2ecc60f6cc5e8ca6d11006314a3963d0113247343497febac92f3f32d57133643
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creator Howell, Jennifer M
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description 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.
doi_str_mv 10.1021/jacs.5b10299
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subjects Carbon - chemistry
Hydrogen - chemistry
Nitrogen - chemistry
Oxidation-Reduction
title Remote Oxidation of Aliphatic C–H Bonds in Nitrogen-Containing Molecules
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