Prev. Article Next Article Table of Contents Remote Oxidation of Aliphatic C–H Bonds in Nitrogen-Containing Molecules
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States
J. Am. Chem. Soc., 2015, 137 (46), pp 14590–14593
DOI: 10.1021/jacs.5b10299
Publication Date (Web): November 4, 2015
Copyright © 2015 American Chemical Society
Abstract
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.
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