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Journals / Journal of the Turkish Chemical Society Section A: Chemistry / 2018 / Cilt: 5 - Sayı: 2

Palladium(II) Complexes of Monodentate Phosphine Ligands and Their Application as Catalyst in Suzuki-Miyaura C-C Coupling Reaction at Room Temperature

Mustafa Kemal YILMAZ
Simay İNCE
Pages
895–902
Publication Date
2018-01-01
DOI
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Sterically hindered and electronically deactivated aryl bromides as well as activated ones gave the corresponding coupling products in good to excellent yields at room temperature.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:A series of palladium(II) complexes from monodentate phosphine ligands (1a-4a) were successfully prepared and characterized with 1H, 31P, 13C NMR, and HRMS techniques.
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Key Findings & Data:These pre-catalysts were applied for the Suzuki-Miyaura C-C coupling reaction of phenylboronic acid with bromobenzene and the influence of the base and solvent on the performance of the pre-catalysts was investigated.
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Conclusion & Impact:Sterically hindered and electronically deactivated aryl bromides as well as activated ones gave the corresponding coupling products in good to excellent yields at room temperature.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Palladium · catalyst · phosphine

Abstract

A series of palladium(II) complexes from monodentate phosphine ligands (1a-4a) were successfully prepared and characterized with 1H, 31P, 13C NMR, and HRMS techniques. These pre-catalysts were applied for the Suzuki-Miyaura C-C coupling reaction of phenylboronic acid with bromobenzene and the influence of the base and solvent on the performance of the pre-catalysts was investigated. Sterically hindered and electronically deactivated aryl bromides as well as activated ones gave the corresponding coupling products in good to excellent yields at room temperature.

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Cite This Article

YILMAZ, M. K., İNCE, S. (2018). Palladium(II) Complexes of Monodentate Phosphine Ligands and Their Application as Catalyst in Suzuki-Miyaura C-C Coupling Reaction at Room Temperature. Journal of the Turkish Chemical Society Section A: Chemistry, Cilt: 5 - Sayı: 2, 895–902. https://ajindex.com/articles/781431

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References (8)

  1. Dounay AB, Overman LE. The Asymmetric Intramolecular Heck Reaction in Natural Product Total Synthesis. Chem. Rev. 2003; 103:2945-63. Tsuji J. Palladium Reagents and Catalysts; Wiley: New York, 2004; Chapter 3:105. Yin L, Liebscher J. Carbon-Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts. Chem. Rev. 2007; 107:133-73.
  2. Polshettiwar V, Decottignies A, Len C, Fihri A. Suzuki–Miyaura Cross‐Coupling Reactions in Aqueous Media: Green and Sustainable Syntheses of Biaryls. ChemSusChem. 2010; 3:502–22. Suzuki A. Cross-Coupling Reactions of Organoboranes: An Easy Way To Construct C-C Bonds (Nobel Lecture). Angew. Chem. Int. Ed. 2011; 50:6723-37.
  3. Mahamo T, Mogorosi MM, Moss JR, Mapolie SF, Slootweg JC, Lammertsma K, and Smith GS. Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki Miyaura coupling catalysts. J. Organomet. Chem. 2012; 703:34-42.
  4. Zhao F, Xin L, Zhang Y, Jia X. Monodentate phosphorus-coordinated palladium(II) complexes as new catalyst for Mizoroki-Heck reaction of aryl halides with electron-deficient olefins. Chinese Chemical Letters. 2018; 29; 493-96.
  5. Sabouncheia SJ, Hosseinzadeha M, Jevinani MZ. Monodentate palladium(0)-[60]fullerene complexes of diphosphine ligands as efficient and sustainable nanocatalysts for Mizoroki-Heck coupling reaction of aryl chlorides. New J. Chem. 2017; 41: 9701-09.
  6. Huang P, Hong FE. Amination and Suzuki coupling reactions catalyzed by palladium complexes coordinated by cobalt-containing monodentate phosphine ligands with bis-trifluoromethyl substituents on bridged arylethynyl: Observation of some unusual metal-containing compounds. J. of Org. Chem. 2009; 694:113–21. Armarego WLE, and Chai CLL. Purficiation of laboratory chemicals; Oxford: Pergamon Press. 2003; Chapter 5. Laue S, Greiner L, Wöltinger J, Liese A. Continuous Application of Chemzymes in a Membrane Reactor: Asymmetric Transfer Hydrogenation of Acetophenone. Adv. Synt. Catal. 2001; 343: 711-20.
  7. Ros A, Estepa B, Bermejo A, Álvarez E, Fernández R, Lassaletta JM. Phosphino hydrazones as suitable ligands in the asymmetric Suzuki-Miyaura cross-coupling. J Org Chem. 2012; 77(10): 4740–50. Yılmaz MK. Palladium(II) complexes with new bidentate phosphine-imine ligands for the Suzuki C-C coupling reactions in supercritical carbon dioxide. J. of Supercritical Fluids. 2018; 138: 221-27.
  8. Yılmaz MK, Güzel B. Iminophosphine palladium(II) complexes: synthesis, characterization, and applicat