Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis

Org Lett. 2018 Nov 16;20(22):7345-7350. doi: 10.1021/acs.orglett.8b03345. Epub 2018 Nov 8.

Abstract

A photocatalytic method for the oxyamination of alkenes using simple nucleophilic nitrogen atom sources in place of prefunctionalized electrophilic nitrogen atom donors is reported. Copper(II) is an inexpensive, practical, and uniquely effective terminal oxidant for this process. In contrast to oxygen, peroxides, and similar oxidants commonly utilized in non-photochemical oxidative methods, the use of copper(II) as a terminal oxidant in photoredox reactions avoids the formation of reactive heteroatom-centered radical intermediates that can be incompatible with electron-rich functional groups. As a demonstration of the generality of this concept, it has been shown that diamination and deoxygenation reactions can also be accomplished using similar photooxidative conditions.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry*
  • Amination
  • Catalysis
  • Copper / chemistry*
  • Hydroxylation
  • Molecular Structure
  • Oxidants / chemistry*
  • Oxidation-Reduction
  • Oxygen / chemistry*
  • Salts

Substances

  • Alkenes
  • Oxidants
  • Salts
  • Copper
  • Oxygen