Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds

J Am Chem Soc. 2014 Sep 24;136(38):13194-7. doi: 10.1021/ja508165a. Epub 2014 Sep 15.

Abstract

9-Methylacridine was identified as a generally effective ligand to promote a Pd(II)-catalyzed C(sp(3))-H and C(sp(2))-H alkylation of simple amides with various alkyl iodides. This alkylation reaction was applied to the preparation of unnatural amino acids and geometrically controlled tri- and tetrasubstituted acrylic acids.

Publication types

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

MeSH terms

  • Acridines / chemistry
  • Acrylates / chemical synthesis
  • Acrylates / chemistry
  • Alkylation
  • Amides / chemistry*
  • Catalysis
  • Iodides / chemistry*
  • Ligands
  • Palladium / chemistry*

Substances

  • Acridines
  • Acrylates
  • Amides
  • Iodides
  • Ligands
  • N-methylacridine
  • Palladium