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

Year 2018, Volume: 5 Issue: 2, 895 - 902, 01.01.2018

Mustafa Kemal Yılmaz , Simay İnce

https://doi.org/10.18596/jotcsa.435122

Cited By: 3

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.

Keywords

Palladium, catalyst, phosphine, Suzuki-Miyaura C-C coupling

References

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• Yılmaz MK, Güzel B. Iminophosphine palladium(II) complexes: synthesis, characterization, and application in Heck cross-coupling reaction of aryl bromides. Appl. Organometal. Chem. 2014; 28:529-36.
• Drew D, Doyle JR, and Shaver AG. Cyclic Diolefin Complexes of Platinum and Palladium. Inorganic Syntheses. 2007; 28:348-49.
• Mahalakshmi H, Phadnis PP, Jain VK, Tiekinkh ERT. Synthesis, spectroscopy and structures. 2004;43(November):2287-93.
• Watkins SE, Craig DC, Colbran SB. A palladium(II) complex of a new iminophosphine ligand derived from diethylenetriamine and 2-(diphenylphosphino)benzaldehyde. 2000; 307: 134-38.
• Hong FE, Ho YJ, Chang YC, Huang YL. Synthesis of cobalt-containing monodentate phosphine ligand and application toward Suzuki cross-coupling reactions. J. of Org. Chem. 2005; 690:1249–57.
• Dodds DL, Boele MDK, Strijdonck GPF, Vries JG, Leeuwen PWNM, and Kamer PCJ. Design, Testing and Kinetic Analysis of Bulky Monodentate Phosphorus Ligands in the Mizoroki-Heck Reaction. Eur. J. Inorg. Chem. 2012; 1660-71.
• Cheng YH, Weng CM, Hong FE. Preparation of monodentate phosphinite ligands: their applications in palladium catalyzed Suzuki reactions. Tetrahedron. 2007; 63:12277–85.
• Bedford RB, Hazelwood SL, Horton PN, Hursthouse MB. Orthopalladated phosphinite complexes as high-activity catalystsfor the Suzuki reaction. Dalton Trans. 2003; 4164-4174.
• Bedford RB, Hazelwood SL, Limmert ME, Albisson DA, Draper SM, Scully PN, Coles SJ, Hursthouse MB. Orthopalladated and -platinated Bulky Triarylphosphite Complexes: Synthesis, Reactivity and Application as High‐Activity Catalysts for Suzuki and Stille Coupling Reactions. Chem. Eur. J. 2003; 9:3216-27.
• So CM, Yeung CC, Lau CP, Kwong FYJ. A New Family of Tunable Indolylphosphine Ligands by One-Pot Assembly and Their Applications in Suzuki-Miyaura Coupling of Aryl Chlorides. Org. Chem. 2008; 73:7803-06.
• Mondal M, Begum T, Gogoi PK, Bora U. Gallic Acid Derived Palladium(0) Nanoparticles: An In Situ Formed “Green and Recyclable” Catalyst for Suzuki‐Miyaura Coupling in Water. Chemistry Select. 2016; 1: 4645-51.
• Billingsley K, Buchwald SL. Highly Efficient Monophosphine-Based Catalyst for the Palladium-Catalyzed Suzuki-Miyaura Reaction of Heteroaryl Halides and Heteroaryl Boronic Acids and Esters. J. Am. Chem. Soc. 2007; 129: 3358-66.
• Zapf A, Beller M. Palladium Catalyst Systems for Cross‐Coupling Reactions of Aryl Chlorides and Olefins. Chem. Eur. J. 2001; 7: 2908-15.
• Nobre SM, Monteiro AL. Pd complexes of iminophosphine ligands: A homogeneous molecular catalyst for Suzuki-Miyaura cross-coupling reactions under mild conditions. J. Mol. Cat. A: Chem. 2009; 313:65-73.
• Scrivanti A, Bertoldini M, Matteoli U, Beghetto V, Antonaroli S, Marini A, Crociani B. Highly efficient Heck olefin arylation in the presence of iminophosphine-palladium(0) complexes. Journal of Molecular Catalysis A: Chemical. 2005; 235:12-16.