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

J Am Chem Soc. 2015 Nov 25;137(46):14590-14593. doi: 10.1021/jacs.5b10299. Epub 2015 Nov 13.

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(sp(3))-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbon / chemistry
  • Hydrogen / chemistry
  • Nitrogen / chemistry*
  • Oxidation-Reduction

Substances

  • Carbon
  • Hydrogen
  • Nitrogen