Activation of C-H bonds via the merger of photoredox and organocatalysis: a coupling of benzylic ethers with Schiff bases

J Am Chem Soc. 2014 Dec 10;136(49):16986-9. doi: 10.1021/ja5102695. Epub 2014 Dec 2.

Abstract

The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic C-H activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radical-radical coupling with secondary aldimines affords a variety of β-amino ether products in good to excellent yields. Mechanistic studies suggest that a reductive quenching pathway of the photocatalyst is operable.

Publication types

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

MeSH terms

  • Benzyl Compounds / chemistry*
  • Catalysis
  • Ethers / chemical synthesis
  • Ethers / chemistry*
  • Imines / chemistry*
  • Iridium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Oxidation-Reduction
  • Photochemical Processes
  • Schiff Bases / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Benzyl Compounds
  • Ethers
  • Imines
  • Organometallic Compounds
  • Schiff Bases
  • Sulfhydryl Compounds
  • Iridium