2-Ferrocenyl-2-thiazoline as a building block of novel phosphine-free ligands

Dalton Trans. 2013 Sep 7;42(33):11992-2004. doi: 10.1039/c3dt50451d.

Abstract

New 1,2-disubstituted ferrocenes [5(b-j), in which R = -SMe, -SPh, -SiPr, -SiMe3, -SePh, -SnBu3, -B(OH)2, -Me, -I] with a thiazoline ring in the ferrocene backbone using as key intermediate a ferrocenyl Fischer carbene complex were synthesized. The capability of the 2-thiazoline moiety as an ortho-directed metalation group was demonstrated by subsequent quenching of lithium intermediate with several electrophiles, proving to be an excellent method for synthesizing bidentate ligands. The catalytic scope of the [N,S] ligand 5b as the corresponding palladium complex 5b-PdCl(2) in a microwave-promoted Heck reaction was also tested. Results obtained showed better catalytic activity of 5b-PdCl(2) compared to other catalytic systems based on a [N,S] ferrocenyl ligand.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ferrous Compounds / chemical synthesis*
  • Ferrous Compounds / chemistry
  • Ligands
  • Models, Molecular
  • Molecular Conformation
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Palladium / chemistry

Substances

  • 2-ferrocenyl-2-thiazoline
  • Ferrous Compounds
  • Ligands
  • Organometallic Compounds
  • Palladium