Visible Light-Induced Unactivated δ-C(sp3 )-H Amination of Alcohols Catalyzed by Iron

ChemSusChem. 2022 Oct 21;15(20):e202201241. doi: 10.1002/cssc.202201241. Epub 2022 Aug 24.

Abstract

An iron-catalyzed remote C(sp3 )-H amination of alcohols through 1,5-hydrogen atom transfer is developed. This protocol provides a method to generate δ-C(sp3 )-N bonds from primary, secondary, and tertiary alcohols under mild conditions. A wide substrate scope and a good functional group tolerance are presented. Mechanistic studies show that a LMCT course of an Fe-OR species and a chlorine radical-induced hydrogen abstraction of an alcohol are possible to generate the alkoxy radical intermediate.

Keywords: C−H activation; amination; hydrogen transfer; iron; photocatalysis.

MeSH terms

  • Alcohols* / chemistry
  • Amination
  • Catalysis
  • Chlorine
  • Hydrogen / chemistry
  • Iron* / chemistry
  • Light
  • Molecular Structure

Substances

  • Alcohols
  • Iron
  • Chlorine
  • Hydrogen