To develop a luminescent material with high color
purity, luminous efficiency, and stability, we synthesized diketone by
carbonylative Suzuki coupling in the presence of Pd(NHC) complex as the
catalyst. Carbonylative coupling of 4,4’-diiodobiphenyl and
phenylboronic acid was investigated to study in detail the catalytic ability of
the Pd(NHC) complex. Reactions were carried out using both CO and metal
carbonyls. Bis-(1,3-dihydro-1,3-dimethyl-2H-imidazol-2-ylidene) diiodo
palladium was used as the catalytic complex. Reaction products biphenyl-4,4’-diylbis
(phenyl-methanone) 3 and (4’-iodobiphenyl-4-yl)(phenyl) methanone 4were obtained as a result of CO
insertion into the palladium(II)-aryl bond. However, when
pyridine-4-yl boronic acid was used in place of phenylboronic acid as the
starting reagent, synthetic reaction yielding 3 and 4were found not to occur.
Cite this paper
D. Lee, J. Hahn and D. Jung, "Carbonylative Coupling of 4,4’-Diiodobiphenyl Catalyzed by Pd(NHC) Complex," Green and Sustainable Chemistry, Vol. 3 No. 1, 2013, pp. 15-18. doi: 10.4236/gsc.2013.31003.
 Y. Jiang and P. Tu, “Four New Phenones from the Cortexes of Polygalatenuifolia,” Chemical & Pharmaceutical Bulletin, Vol. 53, No. 9, 2005, pp. 1164-1166.
 Nilar, L.-H. D. Nguyen, G. Venkatraman, K.-Y. Sim and L. J. Harrison, “Xanthones and Benzophenones from Garciniagriffithii and Garcinia mangostana,” Phytochemistry, Vol. 66, No. 14, 2005, pp. 1718-1723.
 J. W. Lampe, C. K. Biggers, J. M. Defauw, R. J. Foglesong, S. E. Hall, J. M. Heerding, S. P. Hollinshead, H. Hu, P. F. Hughes, G. E. Jagdmann Jr, M. G. Johnson, Y.-S. Lai, C. T. Lowden, M. P. Lynch, J. S. Mendoza, M. M. Murphy, J. W. Wilson, L. M. Ballas, K. Carter, J. W. Darges, J. E. Davis, F. R. Hubbard and M. L. Stamper, “Synthesis and Protein Kinase Inhibitory Activity of Balanol Analogues with Modified Benzophenone Subunits,” Journal of Medicinal Chemistry, Vol. 45, No. 12, 2002, pp. 2624-2643. doi:10.1021/jm020018f
 S. Rancon, A. Chaboud, N. Darbour, G. Comte, C. Bayet, P.-N. Simon, J. Raymond, A. Di Pietro, P. Cabalion and D. Barron, “Natural and Synthetic Benzophenones: Interaction with the Cytosolic Binding Domain of P-Glycoprotein,” Phytochemistry, Vol. 57, No. 4, 2001, pp. 553-557.
 H. Ito, E. Nishitani, T. Konoshima, M. Takasaki, M. Kozuka and T. Yoshida, “Flavonoid and Benzophenone Glycosides from Coleogyne ramosissima,” Phytochemistry, Vol. 54, No. 7, 2000, pp. 695-700.
 J.-C. Li and T. Nohara, “Benzophenone C-Glucosides from Polygala Telephioides,” Chemical & Pharmaceutical Bulletin, Vol. 48, No. 9, 2000, pp. 1354-1355.
 B. M. O’Keefe, N. Simmons and S. F. Martin, “Carbonylative Cross-Coupling of ortho-Disubstituted Aryl Io dides. Convenient Synthesis of Sterically Hindered Aryl Ketones,” Organic Letters, Vol. 10, No. 22, 2008, pp. 5301-5304. doi:10.1021/ol802202j
 R. F. Heck, “A Synthesis of Diaryl Ketones from Arylmercuric Salts,” Journal of the American Chemical Society, Vol. 90, No. 20, 1968, pp. 5546-5548.
 A. Schoenberg, I. Bartoletti and R. F. Heck, “Palladium-Catalyzed Carboalkoxylation of Aryl, Benzyl, and Vinylic Halides,” Journal of Organic Chemistry, Vol. 39, No. 23, 1974, pp. 3318-3326. doi:10.1021/jo00937a003
 A. Schoenberg and R. F. Heck, “Palladium-Catalyzed Amidation of Aryl, Heterocyclic, and Vinylic Halides,” Journal of Organic Chemistry, Vol. 39, No. 23, 1974, pp. 3327-3331. doi:10.1021/jo00937a004
 J.-J. Brunetand R. Chauvin, “Synthesis of Diarylketones through Carbonylative Coupling,” Chemical Society Reviews, Vol. 24, No. 2, 1995, p. 89.
 Y. Tamaru and M. Kimura, “Reactions of Acylpalladium Derivatives with Organometals and Related Carbon Nucleophiles,” Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2, 2002, pp. 2425-2454.
 V. Farina, V. Krishnamurthy and W. J. Scott, “Stille Reaction,” Organic Reactions, Vol. 50, No. 1, 1997, pp. 1-652.
 S.-K. Kang, T. Yamaguchi, T.-H. Kim and P.-S. Ho, “Copper-Catalyzed Cross-Coupling and Carbonylative Cross-Coupling of Organostannanes and Organoboranes with Hypervalent Iodine Compounds,” Journal of Organic Chemistry, Vol. 61, No. 26, 1996, pp. 9082-9083.
 A. M. Echavarren and J. K. Stille, “Palladium-Catalyzed Coupling of Vinyl Epoxides with Organostannanes,” Journal of the American Chemical Society, Vol. 110, No. 12, 1988, pp. 4039-4041. doi:10.1021/ja00220a054
 J. K. Stille, “The Palladium-Catalyzed Cross-Coupling Reaction of Organotin Reagents with Organic Electrophiles,” Angewandte Chemie International Edition English, Vol. 25, No. 6, 1986, pp. 508-524.
 M. Tanaka, “Unsymmetrical Ketone Synthesis from Organic Halides, Carbon Monoxide, and Organotin Compounds Catalyzed by a Palladium Complex,” Tetrahdron Letters, Vol. 20, No. 28, 1979, pp. 2601-2602.
 V. Sans, A. M. Trzeciak, S. Luis and J. J. Ziolkowski, “PdCl2(P(OPh)(3))(2) Catalyzed Coupling and Carbonylative Coupling of Phenylacetylenes with Aryl Iodides in Organic Solvents and in Ionic Liquids,” Catalysis Letters, Vol. 109, No. 1-2, 2006, pp. 37-41.
 P. J. Tambade, Y. P. Patil, N. S. Nandurkar and B. M. Bhanage, “Copper-Catalyzed, Palladium-Free Carbonylative Sonogashira Coupling Reaction of Aliphatic and Aromatic Alkynes with Iodoaryls,” Synle, No. 6, 2008, pp. 886-888.
 N. Haddad, J. Tan and V. Farina, “Convergent Synthesis of the Quinolone Substructure of BILN 2061 via Carbonylative Sonogashira Coupling/Cyclization,” Journal of Organic Chemistry, Vol. 71, No. 13, 2006, pp. 5031-5034.
 M. S. M. Ahmed and A. Mori, “Carbonylative Sonogashira Coupling of Terminal Alkynes with Aqueous Ammonia,” Organic Letters, Vol. 5, No. 17, 2003, pp. 3057-3060. doi:10.1021/ol035007a
 S. Torii, H. Okomoto, L. H. Xu, M. Sadakane, M. V. Shostakovsky, A. B Ponomaryov and V. N. Kalinin, “Syntheses of Chromones and Quinolones via Pd-Catalyzed Carbonylation of O-Iodophenols and Anilines in the Presence of Acetylenes,” Tetrahdron, Vol. 49, No. 31, 1993, pp. 6773-6784.
 T. Ohe, K. Ohe, S. Uemura and N. Sugita, “Palladium-(0)-Catalyzed Carbonylation of Alkenyl- and Arylborates and Boronic Acids with Carbon Monoxide,” Journal of Organometallic Chemistry, Vol. 344, No. 1, 1988, pp. c5-c7. doi:10.1016/0022-328X(88)80220-1
 T. Ishiyama, H. Kizaki, T. Hayashi, A. Suzuki and N. Miyaura, “Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones,” Journal of Organic Chemistry, Vol. 63, No. 14, 1998, pp. 4726-4731.
 M. B. Andrus, Y. Ma, Y. Zang and C. Song, “Palladium-Imidazolium-Catalyzed Carbonylative Coupling of Aryl Diazonium Ions and Aryl Boronic Acids,” Tetrahedron Letters, Vol. 43, No. 50, 2002, pp. 9137-9140.
 Q. Wang and C. Chen, “Nickel-Catalyzed Carbonylative Negishi Cross-Coupling Reactions,” Tetrahedron Letters, Vol. 49, No. 18, 2008, pp. 2916-2921.
 N. A. Bumagin, A. B. Ponomaryov and I. P. Beletskya, “Ketone Synthesis via Palladium-Catalyzed Carbonylation of Organoaluminium Compounds,” Tetrahedron Letters, Vol. 26, No. 39, 1985, pp. 4819-4822.
 T. Yamamoto, T. Kohara and A. Yamamoto, “Selective Formation of Ketone, Diketone and Aldehyde by the Co Insertion into Nickel-Alkyl Bonds of Dialkylnickel Complexes. A Novel Nickel-Catalyzed Syntheses of Ketones and Tertiary Alcohols from Grignard Reagents, Aryl Halides, and Carbon Monoxide,” Chemistry Letters, Vol. 5, No. 11, 1976, pp. 1217-1220.
 Y. Hatanaka, S. Fukushima and T. Hiyama, “Carbonylative Coupling Reaction of Organofluorosilanes with Organic Halides Promoted by Fluoride Ion and Palldium Catalyst,” Tetrahedron, Vol. 48, No. 11, 1992, pp. 2113-2126. doi:10.1016/S0040-4020(01)88878-5
 Y. Hatanaka and Hiyama T, “Highly Selective Cross-Coupling Reactions of Organosilicon Compounds Mediated by Fluoride Ion and a Palladium Catalyst,” Synlett, Vol. 1991, No. 12, 1991, pp. 845-853.
 Y. Hatanaka and T. Hiyama, “Palladium-Catalyzed Carbonylative Coupling of Arylfluorosilanes with Aryl Iodides. A Convenient Synthesis of Diaryl Ketones,” Chemistry Letters, Vol. 18, No. 11, 1989, pp. 2049-2052.
 E. A. B. Kantchev, C. J. O’Brien and M. G. Organ, “Palladium Complexes of N-Heterocyclic Carbenes as Catalysts for Cross-Coupling Reactions-A Synthetic Chemist’s Perspective,” Angewandte Chemie International Edition, Vol. 46, No. 16, 2007, pp. 2768-2813.
 K. J. Covell and D. S. McGuinness, “Redox Processes Involving Hydrocarbylmetal (N-Heterocyclic Carbene) Complexes and Associated Imidazolium Salts: Ramifications for Catalysis,” Coordination Chemistry Reviews, Vol. 248, No. 7-8, 2004, pp. 671-681.
 W. A. Herrmann, “N-Heterocyclic Carbenes: A New Concept in Organometallic Catalysis,” Angewandte Chemie International Edition, Vol. 41, No. 8, 2002, pp. 1290-1309. doi:10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y
 A. C. Hillier, G. A. Grasa, M. S. Viciu, Lee HM, Yang C and Nolan SP, “Catalytic Cross-Coupling Reactions Mediated by Palladium/Nucleophilic Carbene Systems,” Journal of Organometallic Chemistry, Vol. 653, No. 1-2, 2002, pp. 69-82. doi:10.1016/S0022-328X(02)01154-3
 P. Andrea, P. Gabor, P. Zoltan and K. Laszlo, “Carbonylative and Direct Suzuki-Miyaura Cross-Coupling Reactions with 1-Iodo-Cyclohexene,” Journal of Molecular Catalysis, Vol. 255, No. 1-2, 2006, pp. 97-102.
 L. M. Daniela, M. A. Heiddyand C. S. A. Lucia, “Microwave-Assisted Suzuki Reaction Catalyzed by Pd(0)-PVP Nanoparticles,” Tetrahedron Letters, Vol. 51, No. 52, 2010, pp. 6814-6817. doi:10.1016/j.tetlet.2010.09.145