Synthesis and characterizations of N,N,N ',N '-tetrakis (diphenylphosphino)ethylendiamine derivatives: Use of palladium(II) complex as pre-catalyst in Suzuki coupling and Heck reactions

AKBA O., DURAP F., AYDEMİR M., BAYSAL A., Guemguem B., ÖZKAR S.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.694, no.5, pp.731-736, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 694 Issue: 5
  • Publication Date: 2009
  • Doi Number: 10.1016/j.jorganchem.2008.11.063
  • Journal Name: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.731-736
  • Keywords: Aminophosphine, Suzuki coupling, Heck reaction, Catalysis, Palladium, Platinum, LIGANDS (PH2P)(2)NH DPPA, MIXED-METAL CLUSTERS, COORDINATION CHEMISTRY, ARYL BROMIDES, NONCONVENTIONAL METHODOLOGIES, AMINOPHOSPHINE LIGANDS, AMINATION REACTIONS, CRYSTAL-STRUCTURE, BOND FORMATION, HYDROGENATION
  • Middle East Technical University Affiliated: Yes

Abstract

Oxidation of N,N,N',N'-tetrakis(diphenylphosphino)ethylendiamine (1) with elemental sulfur and selenium gives the corresponding sulfide and selenide, respectively, [(Ph2P(E))(2)NCH2CH2N(P(E)Ph-2)(2)] (E: S 1a, Se 1b). Complexes of 1 [(M2Cl4){(Ph2P)(2)NCH2CH2N(PPh2)(2)}] (M: Ni(II) 1c, Pd(II) 1d, Pt(II) 1e) were prepared by the reaction of 1 with NiCl2 or [MCl2(COD)] (M = Pd, Pt). The new compounds were characterized by NMR, IR spectroscopy and elemental analysis. The catalytic activity of Pd(II) complex 1d was tested in the Suzuki coupling reaction and Heck reaction. The palladium complex 1d catalyses the Heck reaction between styrene and aryl bromides as well as Suzuki coupling reaction between phenylboronic acid and arylbromides affording stilbenes and biphenyls in high yield, respectively. (C) 2008 Elsevier B.V. All rights reserved.