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

Year 2019, Volume: 23 Issue: Special [en], 13 - 20, 01.03.2019

Murat Kaloğlu

https://doi.org/10.19113/sdufenbed.440237

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

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