N-Heterocyclic Carbene/Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions in Aqueous Medium

Abstract

In this study, a series of ether-functionalized benzimidazolium salts as N-heterocyclic carbene (NHC) ligands were synthesized and their structures characterized by ¹H NMR, ¹³C NMR, FT-IR, and elemental analysis techniques. The in situ formed [PdX₂(NHC)₂] complexes from the interaction of Pd(OAc)₂ with NHC ligands were used as catalyst in the Suzuki-Miyaura cross-coupling reactions between phenylboronic acid and aryl chlorides under mild reaction conditions in aqueous media. In situ formed [PdX₂(NHC)₂] catalysts showed high catalytic activity for electron-donating, electron-drawing or sterically hindered aryl chlorides.

Keywords

• N-Heterocyclic carbene,Palladium,Suzuki-Miyaura cross-coupling,in situ formed catalyst

Sulu Ortamda N-Heterosiklik Karben/Palladyum Katalizli Suzuki-Miyaura Çapraz-Eşleşme Tepkimeleri

Abstract

Bu çalışmada, N-heterosiklik karben (NHC) ligandı olarak bir seri eter-fonksiyonalize benzimidazolyum tuzu sentezlendi ve yapıları ¹H NMR, ¹³C NMR, FT-IR ve element analizi yöntemleri ile karakterize edildi. NHC ligandları ile Pd(OAc)₂’ın etkileşiminden in situ oluşturulan [PdX₂(NHC)₂] kompleksleri, sulu ortamda ve ılımlı koşullar altında fenilboronik asit ve aril klorürlerin Suzuki-Miyaura çapraz-eşleşme tepkimelerinde katalizör olarak kullanıldı. In situ oluşturulan [PdX₂(NHC)₂] katalizörleri, elektron verici, elektron çekici veya sterik engelli aril klorürler için yüksek katalitik aktivite gösterdi.

Keywords

• N-Heterosiklik karben,Palladyum,Suzuki-Miyaura çapraz-eşleşmesi,in situ oluşturulmuş katalizör

References

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