PEPPSI-type N-heterocyclic carbene palladium(II) complexes as catalysts in the direct C5 arylation of furan and thiophene

被引：0

作者：

Atakol, Arda ^{[1
,2
]}

Yigit, Beyhan ^{[3
]}

Akdan, Hasan ^{[3
]}

Evren, Enes ^{[4
]}

Celepci, Duygu Barut ^{[5
]}

Yigit, Murat ^{[6
]}

Aygun, Muhittin ^{[5
]}

Ozdemir, Ismail ^{[4
,7
,8
]}

机构：

[1] Istinye Univ, Fac Pharm, TR-34394 Istanbul, Turkiye

[2] Istinye Univ, Sci & Technol Res Applicat & Res Ctr, TR-34394 Istanbul, Turkiye

[3] Adiyaman Univ, Fac Sci & Arts, Dept Chem, TR-02040 Adiyaman, Turkiye

[4] Inonu Univ, Fac Sci & Arts, Dept Chem, TR-44280 Malatya, Turkiye

[5] Dokuz Eylul Univ, Fac Sci, Dept Phys, TR-35160 Izmir, Turkiye

[6] Adiyaman Univ, Vocat Sch Tech Sci, Dept Chem & Chem Proc Technol, TR-02040 Adiyaman, Turkiye

[7] Inonu Univ, Catalysis Res & Applicat Ctr, TR-44280 Malatya, Turkiye

[8] Inonu Univ, Drug Applicat & Res Ctr, TR-44280 Malatya, Turkiye

来源：

INORGANICA CHIMICA ACTA | 2025年 / 580卷

关键词：

N-heterocyclic carbene; Palladium; PEPPSI complexes; Arylation; Furan and thiophene; DFT; DIRECT C5-ARYLATION; FUNCTIONALIZATION; IMIDAZOLES; LIGANDS; NHC; ANTICANCER; AMINATION; MECHANISM; CHLORIDES; HALIDES;

D O I：

10.1016/j.ica.2025.122612

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

In this study, a series of amine-functionalized benzimidazolium salts and their PEPPSI-type N-heterocyclic carbene (NHC) palladium(II) complexes 3a-e were synthesized and characterized by FT-IR, 1H NMR and 13C NMR spectroscopy, elemental analysis, and mass spectrometry. The molecular and crystal structure of 3c and 3d was confirmed by the single-crystal X-ray diffraction (SC-XRD) method. Structural analysis reveals that the geometries of the PdII centers of the complexes adopt slightly distorted square planar environment. The new palladium complexes were tested as catalysts in the direct C5 arylation of 2-acetylfuran and 2-acetylthiophene with aryl bromides at 120 degrees C in N,N-dimethylacetamide. The arylation reactions proceeded selectively at the C5 position of the heteroaromatic compounds, and the corresponding coupling products were obtained in moderate to good yields by using 1 mol% of the palladium complex. Also, solid computational validation of the experimental results was achieved by geometric optimizations, frontier molecular orbital and molecular electrostatic potential studies, as well as natural bonding orbital analysis utilizing density functional theory.

引用

页数：11