New Pd-PEPPSI complexes bearing meta-cyanobenzyl-Substituted NHC: Synthesis, characterization, crystal structure and catalytic activity in direct C-H arylation of (Hetero)arenes with aryl bromides

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Turker F., Bereket I., Barut Celepci D., Aktaş A., Gök Y.

JOURNAL OF MOLECULAR STRUCTURE, vol.1205, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1205
  • Publication Date: 2020
  • Doi Number: 10.1016/j.molstruc.2019.127608
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Keywords: Direct arylation, 2-iso-propylthiazole, 2-n-butylfuran, 2-n-butylthiophene, Pd-PEPPSI complexes, X-ray diffraction, HETEROCYCLIC CARBENE COMPLEXES, EFFICIENT, FUNCTIONALIZATION, PALLADIUM(II), HETEROARENES, PRECATALYSTS, REACTIVITY
  • Dokuz Eylül University Affiliated: Yes

Abstract

The prestige of the PEPPSI (Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation) complexes in organometallic chemistry is increasing day by day. Herein, the well-defined seven meta-cyanobenzyl-substituted N-heterocyclic carbene (NHC)-Pd(II)-pyridine (Pd-PEPPSI) complexes were synthesized using palladium acetate, which unlike general procedure is a more economical method than palladium chloride. The new Pd-PEPPSI complexes were obtained from the reaction of the cyanobenzyl substituted NHC precursors and palladium acetate in pyridine. The new complexes have been fully characterized by H-1 NMR, C-13 NMR, FTIR spectroscopy and elemental analysis techniques. Also, the X-ray diffraction method was used to determine the single-crystal structure of a complex. The Pd-PEPPSI complexes have been examined as catalysts in the direct arylation reactions of 2-n-butylfuran and 2-n-butylthiophene with aryl bromide. All complexes have demonstrated excellent activity in these reactions. The Molecular and crystal structure of one of the cyanobenzyl substituted Pd-PEPPSI complexes was determined by the single-crystal X-ray diffraction method. X-ray diffraction studies show that the molecular structure adopts a slightly distorted square-planar geometry with the palladium (II) center. (c) 2019 Elsevier B.V. All rights reserved.