2-Hydroxyethyl-Substituted Pd-PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki-Miyaura Reaction for Aryl Chlorides in Aqueous Media

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Aktaş A., Barut Celepci D., Gök Y., Aygün M.

CHEMISTRYSELECT, vol.3, no.35, pp.9974-9980, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 3 Issue: 35
  • Publication Date: 2018
  • Doi Number: 10.1002/slct.201802046
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.9974-9980
  • Keywords: N-Heterocyclic carbenes, Pd-PEPPSI complexes, Phenylboronic acid, Suzuki-Miyaura reaction, X-ray diffraction, N-HETEROCYCLIC CARBENE, CROSS-COUPLING REACTIONS, DIRECT ARYLATION, AEROBIC CONDITIONS, PALLADIUM, NHC, LIGANDS, PRECATALYSTS, HALIDES, GREEN
  • Dokuz Eylül University Affiliated: Yes

Abstract

In recent years, PEPPSI (Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation) complexes have attracted attention in organometallic chemistry. This study contains the synthesis of the 2-hydroxyethyl-substituted Pd-PEPPSI complexes and their catalytic activity in the Suzuki-Miyaura reaction aryl chlorides in aqueous media. The Pd-PEPPSI complexes have been prepared from the 2- hydroxyethyl-substituted N-heterocyclic carbene (NHC) precursors, palladium chloride and 3-chloropyridine. The Pd-PEPPSI complexes have been characterized by using (HNMR)-H-1, (CNMR)-C-13, FTIR spectroscopy and elemental analysis techniques. The Pd-PEPPSI complexes have been examined as catalysts in the Suzuki-Miyaura reactions in aqueous media with arylboronic acid derivatives. Also, they have demonstrated excellent activity in these reactions. Molecular and crystal structure of one of the 2-hydroxyethyl substituted Pd-PEPPSI complex was determined by single crystal X-ray diffraction method. X-ray studies show that the molecular structure adopts a slightly distorted square-planar geometry with the palladium (II) center.