Synthesis, Structural Characterization, Catalytic Activity on Suzuki-Miyaura and Mizoroki-Heck Coupling Reaction of Dichloro[1-(2-metil-2-propenil)-3-(3,4,5- trimethoxybenzyl) benzimidazole-2-ylidene] pyridine palladium(II) Complex

Abstract

N-heterocyclic carbene-metal complexes exhibit high activity as catalysts. Synthesis of new catalysts and their use in organic synthesis reactions is one of the most important work areas of coordination chemistry. In this study, with the goal of achieving highly efficient palladium catalyzed cross-coupling reactions under mild reaction conditions, 1-(2-metil-2-propenil-3-(3,4,5-
trimethoxybenzyl)benzimidazoliumchloride salt (1) and its Pd(II)-N-heterocyclic carbene complex (2) were synthesized. Structures of obtained both compounds characterized by elemental analysis, FT-IR, 1H NMR and 13C NMR spectroscopies. Afterward, Pd(II)-NHC (2) complex was investigated catalytic activities on SuzukiMiyaura and Mizoroki-Heck coupling reactions. It was observed that synthesized dichloro[1-(2-metil-2-propenil)-3-(3,4,5-trimethoxybenzyl)benzimidazole-2- ylidene]pyridine palladium(II) complex exhibited quite high activity on SuzukiMiyaura coupling reaction at water/isopropyl alcohol mixture

Keywords

• N-heterocyclic carbene
• Palladium
• Suzuki-Miyaura
• Mizoroki-Heck

Dikloro [1-(2-metil-2-propenil)-3-(3,4,5-trimetoksibenzil) benzimidazol-2-iliden] piridin paladyum(II) Kompleksinin Sentezi, Yapısal Karakterizasyonu, Suzuki-Miyaura ve Mizoroki-Heck Eşleşme Tepkimelerindeki Katalitik Aktivitesi

Abstract

N-heterosiklik karben-metal kompleksleri katalizör olarak yüksek aktivite göstermektedirler. Yeni katalizörlerin sentezlenmesi ve organik sentez tepkimelerinde kullanılması koordinasyon kimyasının en önemli çalışma alanlarından biridir. Bu çalışmada, ılımlı tepkime koşulları altında, yüksek verimli paladyum katalizli eşleşme tepkimelerini gerçekleştirmek amacıyla, 1-(2-metil-2-propenil)-3-(3,4,5-trimetoksibenzil)benzimidazolyum klorür tuzu (1)  ve bu yeni tuzdan Pd(II)-N-heterosiklik karben kompleksi (NHC) (2) sentezlendi. Elde edilen her iki bileşiğin yapısı elementel analiz, FT-IR, ¹H NMR ve ¹³C NMR spektroskopileri ile karakterize edildi. Daha sonra Pd(II)-NHC (2) kompleksinin Suzuki-Miyaura ve Mizoroki-Heck eşleşme tepkimelerindeki katalitik aktivitesi incelendi. Sentezlenen dikloro[1-(2-metil-2-propenil)-3-(3,4,5-trimetoksibenzil) benzimidazol-2-iliden] piridin paladyum(II) kompleksinin Suzuki-Miyaura eşleşme tepkimesi için su-izopropil alkol karışımında oldukça yüksek aktivite gösterdiği gözlendi.

Keywords

• N-heterosiklik karben
• Paladyum
• Suzuki-Miyaura
• Mizoroki-Heck

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