Synthesis, characterization and the Suzuki–Miyaura coupling reactions of N-heterocyclic carbene–Pd(II)–pyridine (PEPPSI) complexes

Yaşar, Sedat; Şahin, Çağlar; Arslan, Murat; Özdemır, İsmaıl

doi:10.1016/j.jorganchem.2014.10.047

Cited by 74 publications

(24 citation statements)

References 74 publications

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“…The chemical shifts for the carbon atom fall in the range 174.3–198.8 ppm and are similar to those found for other palladium–carbene complexes. These complexes show typical spectroscopic signatures, which are in line with those recently reported for other [PdCl 2 (N‐heterocyclic carbene) 2 ] complexes . The analytical data are in good agreement with the compositions proposed for all the complexes and are summarized in Table .…”

Section: Resultssupporting

confidence: 89%

Synthesis of palladium complexes derived from imidazolidin‐2‐ylidene ligands and used for catalytic amination reactions

Karaca

Gürbüz

Şahın

et al. 2016

Applied Organom Chemis

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N‐Aryl amination and the Buchwald–Hartwig reaction are of great synthetic and industrial interest and scientists accept their usefulness and versatility for obtaining arylamines. In this study Ag–N‐heterocyclic carbene complexes were used as transmetallation reagents for the synthesis of Pd–N‐heterocyclic carbene complexes. The new Pd–N‐heterocyclic carbene complexes were characterized using elemental analysis and 1H NMR, 13C NMR and infrared spectroscopies. The crystal structure of one, namely dichlorobis[1,3‐bis(2‐methylbenzyl)imidazolidin‐2‐yliden]palladium(II), is presented. The activity of the Pd(II) complexes in the coupling reaction of anilines or amines with bromobenzene was investigated. These complexes exhibited high catalytic activities in the direct synthesis of triarylamines and secondary amines in a single step. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Resultssupporting

confidence: 89%

Synthesis of palladium complexes derived from imidazolidin‐2‐ylidene ligands and used for catalytic amination reactions

Karaca

Gürbüz

Şahın

et al. 2016

Applied Organom Chemis

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“…The FT‐IR data clearly indicated the presence of ν (OH) at 3431, 3475, 3458, 3347, 3408, 3438, 3397, 3469, 3465 and 3230 cm −1 for the (NHC)PdI 2 (pyridine) complexes ( 1 a‐j ), respectively. These NMR and FT‐IR data are consistent with literature ,. The results of the elemental analysis were evaluated and it was observed that the calculated values were very close to the found values.…”

Section: Resultsmentioning

confidence: 99%

2‐hydroxyethyl‐substituted (NHC)PdI₂(pyridine) (Pd‐PEPPSI) Complexes: Synthesis, Characterization and the Catalytic Activity in the Sonogashira Cross‐coupling Reaction

et al. 2019

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Here, new series of the 2‐hydroxyethyl‐substituted (NHC)PdI2(pyridine) (Pd‐PEPPSI) complexes have been synthesized. These complexes have been prepared from the 2‐hydroxyethyl‐substituted N‐heterocyclic carbene (NHC) precursors, palladium chloride and pyridine. The synthesized Pd‐PEPPSI complexes have been characterized by using 1H NMR, 13C NMR, FTIR spectroscopy and elemental analysis techniques. The catalytic activity of the 2‐hydroxyethyl‐substituted Pd‐PEPPSI complexes has been examined in the Sonogashira cross‐coupling reaction by using phenylacetylene and aryl bromide. The Pd‐PEPPSI complexes have demonstrated great activity in the Sonogashira cross‐coupling reaction. The molecular and crystal structures of the three of the Pd‐PEPPSI complexes were determined by single‐crystal X‐ray diffraction method. X‐ray studies show that all the molecular structures adopt slightly distorted square‐planar geometry around the palladium (II) center.

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“…In 2015, Yasar and co‐workers reported a new series of air and moisture‐stable NHC–PdCl 2 –pyridine complexes ( C196 ) in 80–92% yields as shown in Scheme . The catalytic activity of ( C196 ) for the Suzuki cross‐coupling of aryl halides under mild conditions in aqueous DMF was also investigated.…”

Section: N‐heterocyclic Carbenes As Ligands and Their Metal Complexesmentioning

confidence: 99%

Recent Advances in the Schiff Bases and N‐Heterocyclic Carbenes as Ligands in the Cross‐Coupling Reactions: A Comprehensive Review

Kumar

2019

Journal of Heterocyclic Chem

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Cross‐coupling reactions, namely, the Suzuki–Miyaura, Heck, Sonogashira, Hiyama, Negishi, Kumada, and Hartwig–Buchwald, are the most powerful approaches in the formation of C–C, C–N, C–O, and C–S bonds for the complex organic scaffolds in drugs, natural products, organic materials, and fine chemicals. The nitrogen‐based ligands have upper hands in these reactions because they are air stable, inexpensive, and easier to handle than the phosphorous counterparts. In this perspective, Schiff bases and N‐heterocyclic carbenes have been explored extensively in terms of novel design and preparation as ligands in the coupling reactions. Facile recovery and reusability of these ligands make them eco‐friendly and economical. A comprehensive outline on the progress in Schiff bases–metal complexes and NHC–metal complexes that mediated cross‐coupling reactions with recent examples highlighted is reported (160 references).

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Synthesis, characterization and the Suzuki–Miyaura coupling reactions of N-heterocyclic carbene–Pd(II)–pyridine (PEPPSI) complexes

Cited by 74 publications

References 74 publications

Synthesis of palladium complexes derived from imidazolidin‐2‐ylidene ligands and used for catalytic amination reactions

Synthesis of palladium complexes derived from imidazolidin‐2‐ylidene ligands and used for catalytic amination reactions

2‐hydroxyethyl‐substituted (NHC)PdI₂(pyridine) (Pd‐PEPPSI) Complexes: Synthesis, Characterization and the Catalytic Activity in the Sonogashira Cross‐coupling Reaction

Recent Advances in the Schiff Bases and N‐Heterocyclic Carbenes as Ligands in the Cross‐Coupling Reactions: A Comprehensive Review

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Synthesis, characterization and the Suzuki–Miyaura coupling reactions of N-heterocyclic carbene–Pd(II)–pyridine (PEPPSI) complexes

Cited by 74 publications

References 74 publications

Synthesis of palladium complexes derived from imidazolidin‐2‐ylidene ligands and used for catalytic amination reactions

Synthesis of palladium complexes derived from imidazolidin‐2‐ylidene ligands and used for catalytic amination reactions

2‐hydroxyethyl‐substituted (NHC)PdI2(pyridine) (Pd‐PEPPSI) Complexes: Synthesis, Characterization and the Catalytic Activity in the Sonogashira Cross‐coupling Reaction

Recent Advances in the Schiff Bases and N‐Heterocyclic Carbenes as Ligands in the Cross‐Coupling Reactions: A Comprehensive Review

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2‐hydroxyethyl‐substituted (NHC)PdI₂(pyridine) (Pd‐PEPPSI) Complexes: Synthesis, Characterization and the Catalytic Activity in the Sonogashira Cross‐coupling Reaction