Efficient Mizoroki–Heck coupling reactions using phosphine-modified Pd(II)–picolinate complex

References

• (a) Heck, R. F. Palladium-Catalyzed Reactions of Organic Halides with Olefins. Acc. Chem. Res. 1979, 12, 146. DOI: 10.1002/chin.197937153; (b) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Masciocchi, N.; Sottocornola, S. New 4-Spiroannulated Tetrahydroisoquinolines by a One-Pot Sequential Procedure. Isolation and Characterization of σ-Alkylpalladium Heck Intermediates. Org. Lett. 2006, 8, 4521; (c) Clique, B.; Fabritius, C.; Couturier, C.; Monteiro, N.; Balme, G. Unexpected Isolation, and Structural Characterization, of a β-Hydrogen-Containing σ-Alkylpalladium Halide Complex in the Course of an Intramolecular Heck Reaction. Synthesis of Polycyclic Isoquinoline Derivatives. Chem. Commun. 2003, 272. DOI: 10.1039/b211856b; (d) Yahiaoui, S.; Fardost, A.; Trejos, A.; Larhed, M. Chelation-Mediated Palladium(II)-Catalyzed Domino Heck−Mizoroki/Suzuki−Miyaura Reactions Using Arylboronic Acids: Increasing Scope and Mechanistic Understanding. J. Org. Chem. 2011, 76, 2433; (e) Beletskaya, I. P.; Cheprakov, A. V. The Heck Reaction as a Sharpening Stone of Palladium Catalysis. Chem. Rev. 2000, 100, 3009. DOI: 10.1021/cr9903048; (f) Rostamnia, S.; Rahmani, T. Ordered Mesoporous SBA-15/PrSO3Pd and SBA-15/PrSO3PdNP as Active, Reusable and Selective Phosphine-Free Catalysts in C-X Activation Heck Coupling Process. Appl. Organometal. Chem. 2015, 29, 471. DOI: 10.1002/aoc.3319.
   Web of Science ®Google Scholar
• (a) Guram, A. S.; Wang, X.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J. New Catalysts for Suzuki−Miyaura Coupling Reactions of Heteroatom-Substituted Heteroaryl Chlorides. J. Org. Chem. 2007, 72, 5104. DOI: 10.1021/jo070341w; (b) Fleckenstein, C. A.; Plenio, H. Aqueous Cross-Coupling: Highly Efficient Suzuki-Miyaura Coupling of N-Heteroaryl Halides and N-Heteroarylboronic Acids. Green Chem. 2007, 9, 1287. DOI: 10.1039/b711965h; (c) Lindhardt, A. T.; Mantel, M. L. H.; Skrydstrup, T. Palladium-Catalyzed Intermolecular Ene-Yne Coupling: Development of an Atom-Efficient Mizoroki-Heck-Type Reaction. Angew. Chem., Int. Ed. 2008, 47, 2668. DOI: 10.1002/ange.200705558; (d) Wu, L.; Li, Z.; Zhang, F.; He, Y.; Fan, Q. Air-Stable and Highly Active Dendritic Phosphine Oxide- Stabilized Palladium Nanoparticles: Preparation, Characterization and Applications in the Carbon-Carbon Bond Formation and Hydrogenation Reactions. Adv. Synth. Catal. 2008, 350, 846; (e) Farina, V. High-Turnover Palladium Catalysts in Cross-Coupling and Heck Chemistry: A Critical Overview. Adv. Synth. Catal. 2004, 346, 1553. DOI: 10.1002/adsc.200404178; (f) Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. On the Nature of the Active Species in Palladium Catalyzed Mizoroki-Heck and Suzuki-Miyaura Couplings - Homogeneous or Heterogeneous Catalysis. A Critical Review. Adv. Synth. Catal. 2006, 348, 609. DOI: 10.1002/adsc.200505473.
   PubMed Web of Science ®Google Scholar
• (a) Billingsley, K.; Buchwald, S. L. 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. DOI: 10.1002/chin.200730073; (b) Lipshutz, B. H.; Taft, B. R. Heck Couplings at Room Temperature in Nanometer Aqueous Micelles. Org. Lett. 2008, 10, 1329. DOI: 10.1021/ol702755g.
   PubMed Web of Science ®Google Scholar
• Kantchev, E. A. B.; O’Brien, C. J.; Organ, M. G. Palladium Complexes of N-Heterocyclic Carbenes as Catalysts for Cross-Coupling Reactions—A Synthetic Chemist’s Perspective. Angew. Chem. Int. Ed. 2007, 16, 2768. DOI: 10.1002/chin.200728241.
   Google Scholar
• Jain, V. K.; Jain, L. The Chemistry of Binuclear Palladium(II) and Platinum(II) Complexes. Coord. Chem. Rev. 2005, 249, 3075–3197. DOI: 10.1016/j.ccr.2005.06.020.
   Web of Science ®Google Scholar
• Andrade, A. P. S.; Arantes, L. M.; Kadooca, J. Y.; Carvalho, R. L.; de Fa´tima, A.; Sabino, A. A. Palladium Complexes with Tetradentate Schiff Bases or their Corresponding Amines: Synthesis and Application in Heck Reactions. ChemistrySelect. 2016, 5, 886. DOI: 10.1002/slct.201600244.
   Web of Science ®Google Scholar
• Wanga, Y.; Yang, Q.; Yang, L.; Shi, J.; Zhang, M. A Novel N–O Ligand for Palladium-Catalyzed Mizoroki–Heck Reaction in Neat Water. Tetrahedron Lett. 2013, 54, 5314–5317. DOI: 10.1016/j.tetlet.2013.07.097.
   Web of Science ®Google Scholar
• Cui, X.; Li, J.; Zhang, Z-P.; Fu, Y.; Liu, L.; Guo, Q-X. Pd(quinoline-8-carboxylate)2 as a Low-Priced, Phosphine-Free Catalyst for Heck and Suzuki Reactions. J. Org. Chem. 2007, 72, 9342–9345.
   PubMed Web of Science ®Google Scholar
• Iyer, S.; Kulkarni G. M.; Ramesh, C. Mizoroki – Heck Reaction, Catalysis by Nitrogen Ligand Pd Complexes and Activation of Aryl Bromides. Tetrahedron 2004, 60, 2163–2172.
   Web of Science ®Google Scholar
• (a) Jayasree, S.; Seayad, A.; Chaudhari, R. V. Novel Palladium(II) Complex Containing a Chelating Anionic N−O Ligand: Efficient Carbonylation Catalyst. Org. Lett. 2000, 2(2), 203–206; (b) Sarkar, B. R.; Chaudhari, R. V. Ossification: A New Approach to Immobilize Metal Complex Catalysts—Applications to Carbonylation and Suzuki Coupling Reactions. J. Catal. 2006, 242(1), 231–238. DOI: 10.1016/j.jcat.2006.05.032.
   PubMed Web of Science ®Google Scholar
• Feuerstein, M.; Doucet, H.; Santelli, M. Efficient Heck Vinylation of Aryl Halides Catalyzed by a New Air-Stable Palladium-Tetraphosphine Complex. J. Org. Chem. 2001, 66, 5923. DOI: 10.1021/jo015645b.
   PubMed Web of Science ®Google Scholar
• Najera, C.; Gil-Molto, J.; Karlstro, S.; Falvello, L. R. Di-2-Pyridylmethylamine-Based Palladium Complexes as New Catalysts for Heck, Suzuki, and Sonogashira Reactions in Organic and Aqueous Solvents. Org. Lett. 2003, 5(9), 1451.
   PubMed Web of Science ®Google Scholar