Carbonylative Coupling of 4,4’-Diiodobiphenyl Catalyzed by Pd(NHC) Complex

Do-Hun Lee, Jung-Tai Hahn, Dai-Il Jung

Department of Beautycare, Youngdong University, Youngdong, South Korea.
Department of Chemistry, Dong-A University, Busan, South Korea.

DOI: 10.4236/gsc.2013.31003                

Abstract

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 4 were 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 4 were found not to occur.

Keywords

Carbonylative Coupling; Metal Carbonyl; Pd(NHC) Complex; 4, 4’-Diiodobiphenyl; Phenylboronic Acid

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Y. Jiang and P. Tu, “Four New Phenones from the Cortexes of Polygalatenuifolia,” Chemical & Pharmaceutical Bulletin, Vol. 53, No. 9, 2005, pp. 1164-1166. doi:10.1248/cpb.53.1164
[2]	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. doi:10.1016/j.phytochem.2005.04.032
[3]	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
[4]	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. doi:10.1016/S0031-9422(01)00120-0
[5]	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.
[6]	J.-C. Li and T. Nohara, “Benzophenone C-Glucosides from Polygala Telephioides,” Chemical & Pharmaceutical Bulletin, Vol. 48, No. 9, 2000, pp. 1354-1355. doi:10.1248/cpb.48.1354
[7]	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
[8]	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. doi:10.1021/ja01022a040
[9]	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
[10]	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
[11]	J.-J. Brunetand R. Chauvin, “Synthesis of Diarylketones through Carbonylative Coupling,” Chemical Society Reviews, Vol. 24, No. 2, 1995, p. 89. doi:10.1039/cs9952400089
[12]	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.
[13]	V. Farina, V. Krishnamurthy and W. J. Scott, “Stille Reaction,” Organic Reactions, Vol. 50, No. 1, 1997, pp. 1-652.
[14]	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. doi:10.1021/jo962033w
[15]	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
[16]	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. doi:10.1002/anie.198605081
[17]	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. doi:10.1016/S0040-4039(01)86360-7
[18]	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. doi:10.1007/s10562-006-0053-7
[19]	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.
[20]	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. doi:10.1021/jo060556q
[21]	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
[22]	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. doi:10.1016/S0040-4020(01)80421-X
[23]	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
[24]	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. doi:10.1021/jo980417b
[25]	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. doi:10.1016/S0040-4039(02)02186-X
[26]	Q. Wang and C. Chen, “Nickel-Catalyzed Carbonylative Negishi Cross-Coupling Reactions,” Tetrahedron Letters, Vol. 49, No. 18, 2008, pp. 2916-2921. doi:10.1016/j.tetlet.2008.03.035
[27]	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. doi:10.1016/S0040-4039(00)94960-8
[28]	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. doi:10.1246/cl.1976.1217
[29]	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
[30]	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. doi:10.1055/s-1991-20899
[31]	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. doi:10.1246/cl.1989.2049
[32]	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. doi:10.1002/anie.200601663
[33]	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. doi:10.1016/j.ccr.2004.02.006
[34]	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
[35]	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
[36]	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. doi:10.1016/j.molcata.2006.03.070
[37]	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