N,N,N ',N '-Tetrakis(2-hydroxyethyl)ethylenediamine palladium(II) complex as efficient catalyst for the Suzuki/Miyaura reaction in water

GÜLCEMAL S., KANİ İ., Yilmaz F., Cetinkaya B.

TETRAHEDRON, vol.66, no.30, pp.5602-5606, 2010 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 66 Issue: 30
  • Publication Date: 2010
  • Doi Number: 10.1016/j.tet.2010.05.092
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Current Chemical Reactions (CCR)
  • Page Numbers: pp.5602-5606
  • Keywords: Suzuki/Miyaura reaction, Palladium, EdteH(4), Water, CROSS-COUPLING REACTIONS, UNUSUAL STRUCTURAL TYPES, CRYSTAL-STRUCTURE, ROOM-TEMPERATURE, MOLECULAR-MECHANICS, ARYL BROMIDES, AQUEOUS-MEDIA, SUZUKI, LIGANDS, PALLADACYCLES
  • Anadolu University Affiliated: Yes

Abstract

A new water soluble palladium(II) complex (2) derived from N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine (edteH(4)) (1) was synthesized in high yield and characterized by H-1, C-13, HMQC and COSY NMR spectroscopy. X-ray diffraction studies on a single crystal of 2 confirmed the cis square planar geometry; the edteH(4) ligand (1) is kappa(2) (N,N)-coordinated with four pendant CH2CH2OH groups. This new complex [PdCl2(edteH(4))] (2) and the previously synthesized triethanolamine complex [Pd(OCH2CH2N (CH2CH2OH)(2))(2)] (3) were tested as catalysts for the Suzuki/Miyaura cross-coupling reaction of various aryl bromides with phenylboronic acid in water. Electronically activated aryl bromides, such as 4-bromoacetophenone and 4-bromobenzaldehyde undergo the cross-coupling with extremely high turnover numbers (TON) of up to 1,00,000 without organic solvent. (C) 2010 Elsevier Ltd. All rights reserved.