Synthesis and characterization of transition metal complexes of thiophene-2-methylamine: X-ray crystal structure of palladium (II) and platinum (II) complexes and use of palladium(II) complexes as pre-catalyst in Heck and Suzuki cross-coupling reactions


AYDEMİR M., BAYSAL A., DURAP F., Gumgum B., ÖZKAR S., Yildirim L. T.

APPLIED ORGANOMETALLIC CHEMISTRY, vol.23, no.11, pp.467-475, 2009 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 23 Issue: 11
  • Publication Date: 2009
  • Doi Number: 10.1002/aoc.1547
  • Title of Journal : APPLIED ORGANOMETALLIC CHEMISTRY
  • Page Numbers: pp.467-475
  • Keywords: aminophosphine, bis(phosphino)amine, palladium, Heck reaction, Suzuki coupling, COORDINATION CHEMISTRY, C-H, DERIVATIVES APPLICATION, LIGANDS, RUTHENIUM(II), ARYL, PHOSPHINITE, ELIMINATION, ACTIVATION, VANCOMYCIN

Abstract

The reactions of thiophene-2-(N-diphenylphosphino)methylamine, Ph2PNHCH2-C4H3S, 1 and thiophene-2-[N,N-bis(diphenylphosphino)methylamine], (Ph2P)(2)NCH2-C4H3S, 2, with MCl2(cod) (M = Pd, Pt; cod = 1,5-cyclooctadiene) or [Cu(CH3CN)(4)]PF6 yields the new complexes [M(Ph2PNHCH2-C4H3S)(2)Cl-2], M = Pd 1a, Pt 1 b, [Cu(Ph2PNHCH2-C4H3S)(4)]PF6, 1c, and [M(Ph2P)(2)NCH2-C4H3S)Cl-2], M = Pd 2a, Pt 2b, (Cu[(Ph2P)(2)NCH2-C4H3S](2))PF6, 2c, respectively. The new compounds were isolated as analytically pure crystalline solids and characterized by (31)p-, C-13-, H-1-NMR and IR spectroscopy and elemental analysis. Furthermore, the solid-state molecular structures of representative palladium and platinum complexes of bis(phosphine)amine, 2a and 2b, respectively, were determined using single crystal X-ray diffraction analysis. The palladium complexes were tested as potential catalysts in the Heck and Suzuki cross-coupling reactions. Copyright (C) 2009 John Wiley & Sons, Ltd.