N, N, N', N'-Tetramethylethylenediamine-Enabled Photoredox-Catalyzed C-H Methylation of N-Heteroarenes

J Org Chem. 2021 Sep 3;86(17):11905-11914. doi: 10.1021/acs.joc.1c01325. Epub 2021 Aug 3.

Abstract

Aiming at the valuable methylation process, readily available and inexpensive N,N,N',N'-tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Ethylenediamines*
  • Methylation
  • Protons*

Substances

  • Ethylenediamines
  • Protons
  • N,N,N',N'-tetramethylethylenediamine