Cross-Coupling Catalysts Novel Boronic Acids/Esters Intermediates
Overview Patents Publications Presentations


Air- Stable Palladium-Catalyzed Suzuki Cross-Coupling Reaction

General Procedure for Suzuki Reactions

POPd (50.0 mg, 0.10 mmol), chlorobenzene (1.13 g, 10.0 mmol), Me-C6H4B(OH)2 (2.04 g, 15.0 mmol), and K2CO3 (4.15 g, 30.0 mmol) were weighed in air and transferred to a 50 mL of reactor equipped with magnetic stir bar and 10 mL of THF. The reaction mixture was refluxed under nitrogen or open-to-air condition for 2 h. The reaction was diluted with 300 mL of hexane and 100 mL of H2O. The layers were separated, and organic layer was washed with H2O (100 mL), brine (100 mL), and dried over MgSO4, filtered, and solvents removed from the filtrate by rotary evaporation. The resulting residue was chromatographed on silica gel using hexane as eluant. The eluate was concentrated by rotary evaporation followed by high vacuum to give 1.59 g (95% yield) of 4-phenyltoluene.

References

  1. Org. Lett., 2009, 11(2), 381-384.
    Yang, D. X.; Colletti, S. L.; Wu, K.; Song, M.; Li, George. Y. and Shen, H. C. “Palladium-Catalyzed Suzuki-Miyaura Coupling of Pyridyl-2-boronic Esters with Aryl Halides Using Highly Active and Air-Stable Phosphine Chloride and Oxide Ligands”.
  2. Org. Lett., 2009, 11(2), 345-347.
    Deng, J. Z.; Paone, D. V.; Ginnetti, A. T.; Kurihara, H.; Dreher, S. D.; Weississman, S.A.; Stauffer, S.R. and Burgey, C. S. “Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates”.
  3. Eur. J. Med. Chem., 2006, 1827-1835.
    Shaughnessy, K. H. “Beyond TPPTS: New Approaches to the Development of Efficient Palladium-Catalyzed Aqueous-Phase Cross-Coupling Reactions”.
  4. Chem. Commun., 2006, 4814-4816.
    Fitzmaurice, R. J., Etheridge, Z. C., Jumel, E., Woolfson, D. N., Caddick, S. “Microwave Palladium Catalysed Coupling Reactions: A Diversity-Oriented Synthesis Approach to Functionalised Flavones”.
  5. Eur. J. Med. Chem., 2006, 1917-1925.
    Wolf, C. and Ekoue-Kovi, K. “Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Using Phosphinous Acids and Dialkyl(chloro)phosphane Ligands”.
  6. ChemInform, 2006, 37(17).
    Wan, Z., et al. “A highly Convergent Synthesis of 2-Phenyl Quinoline as Dual Antagonists for NK2 and NK3 Receptors”.
  7. J. Med. Chem., 2005, 48, 3930-3934.
    Khanapure, S. P., etc. "3-[4-(Methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl)Phenyl Ketone as a Potent and Orally Active Cyclooxygenase-2 Selective Inhibitor: Synthesis and Biological Evaluation”.
  8. Synthesis. 2005, 2287-2292.
    Lerebours, R., Wolf, C. ““Palladium-Phosphinous Acid Catalyzed Cross-Coupling of Aryl Halides Using a Hypervalent Phenylsilane in Water”.
  9. J. Org. Chem. 2005, 70, 2332-2334.
    Miao, G., Ye, P., Yu, L., and Baldino, C. M., “Microwave-Promoted Suzuki Reactions of Aryl Chlorides in Aqueous Media”.
  10. Synthetic Communications, 2005, 35, 3105-3112. Hongxing Y., Jeffrey K. K., Qi J., Chongjie Z., Mary S. B., James F. C., Douglas W. P. H., Larry J. J., Mark A. L., Henry M. S., Keith W. W., Katherine L. W., Zehong W., “A Highly Convergent Synthesis of 2-Phenyl Quinoline as Dual Antagonists for NK2 and NK3 Receptors”.
  11. Tetrahedron Lett. 2004, 45, 5283-5286.
    Khanapure, S. P., Garvey, D. S., "Use of Highly Reactive, Versatile and Air-Stable Palladium-Phosphinous Acid Complex [(t-Bu)2P(OH)]2PdCl2 (POPd) as a Catalyst for the Optimized Suzuki-Miyaura Cross-Coupling of Less Reactive Heteroaryl Chlorides and Arylboronic Acids".
  12. J. Org. Chem. 2004, 69, 6920-6922.
    Poondra, R. R., Fischer, P. M., Turner, N. J., “Efficient Palladium-Catalyzed Cross-Coupling of -ß-Chloroalkylidene/arylidene Malonates Using Microwave Chemistry”.
  13. Org. lett. 2004, 6, 1147-1150.
    Wolf, C., Lerebours, R., ““Palladium Phosphinous Acid-Catalyzed NaOH-promoted Cross-Coupling Reactions of Arylsiloxanes with Aryl Chlorides and Bromides in Water”.
  14. Synthesis, 2003, 2069-2073.
    Wolf, C.; Lerebours, R.; Tanzini, E. H.“Cross-coupling Reactions of Aryl Chlorides and Bromides with Phenyltrimethoxysilane Catalyzed by Palladium-phosphinous Acid Complexes“
  15. Organic Letters, 2003, 5(17), 3131-3134.
    Yang, W., Wang, Y., Corte, J. R. "Efficient Synthesis of 2-Aryl-6-chloronicotinamides via PXPd2-Catalyzed Regioselective Suzuki Coupling".
  16. J. Org. Chem. 2002, 67(11), 3643-3650.
    Li, George Y. “Highly Active, Air-Stable Palladium Catalysts for the C-C and C-S Bond-Forming Reactions of Vinyl and Aryl Chlorides: Use of Commercially Available [(t-Bu)2POH]2PdCl2, [(t-Bu)2P(OH)PdCl2]2 and {[(t-Bu)2PO•••H•••OP(t-Bu)2]PdCl}2 as Catalysts”.
  17. J. Org. Chem. 2001, 66(25), 8677-8681.
    Li, George Y.; Zheng, G.; Noonan, A. F. “Highly Active, Air-Stable Versatile Palladium Catalysts for the C-C, C-N, and C-S Bond Formations via Cross-Coupling Reactions of Aryl Chlorides”.
  18. Angew. Chem. Int. Ed. 2001, 1513-1516. Li, George Y. “The First Phosphine Oxide Ligand Precursors for Transition Metal Catalyzed Cross-Coupling Reactions: C-C, C-N, and C-S Bond Formation on Unactivated Aryl Chlorides”.



site design.darshana merchant