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

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

1. Dounay AB, Overman LE. The Asymmetric Intramolecular Heck Reaction in Natural Product Total Synthesis. Chem. Rev. 2003; 103:2945-63.
2. Tsuji J. Palladium Reagents and Catalysts; Wiley: New York, 2004; Chapter 3:105.
3. Yin L, Liebscher J. Carbon-Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts. Chem. Rev. 2007; 107:133-73.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.

9. 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.
10. Armarego WLE, and Chai CLL. Purficiation of laboratory chemicals; Oxford: Pergamon Press. 2003; Chapter 5.
11. 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.
12. 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.
13. 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.
14. 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.
15. Drew D, Doyle JR, and Shaver AG. Cyclic Diolefin Complexes of Platinum and Palladium. Inorganic Syntheses. 2007; 28:348-49.
16. Mahalakshmi H, Phadnis PP, Jain VK, Tiekinkh ERT. Synthesis, spectroscopy and structures. 2004;43(November):2287-93.
17. 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.
18. 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.
19. 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.
20. Cheng YH, Weng CM, Hong FE. Preparation of monodentate phosphinite ligands: their applications in palladium catalyzed Suzuki reactions. Tetrahedron. 2007; 63:12277–85.
21. Bedford RB, Hazelwood SL, Horton PN, Hursthouse MB. Orthopalladated phosphinite complexes as high-activity catalystsfor the Suzuki reaction. Dalton Trans. 2003; 4164-4174.
22. 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.
23. 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.
24. 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.
25. 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.
26. Zapf A, Beller M. Palladium Catalyst Systems for Cross‐Coupling Reactions of Aryl Chlorides and Olefins. Chem. Eur. J. 2001; 7: 2908-15.
27. 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.
28. 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.