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A Green, One-Pot Route to the Biphenyldicarboxylic Acids: Useful Intermediates in Polymer Synthesis

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DOI: 10.4236/ijoc.2013.32016    5,804 Downloads   8,267 Views   Citations

ABSTRACT

Isomeric biphenyldicarboxylic acids have been prepared from halobenzoic acids and aryl boronic acids using an inverse biphasic modification of the Suzuki coupling reaction. In this modification of the Suzuki coupling reaction, both reactants and products are contained in the aqueous phase, with palladium catalyst contained in the organic phase. A phase transfer catalyst is used to contact reactants and catalyst. Multiple cycles, in which the catalyst/organic solvent is contacted with fresh aqueous reactants, generating products with no loss of efficiency, are demonstrated. We believe that this is the first demonstration of Suzuki coupling to produce biphenyldicarboxylic acids, in this case useful as monomers for the production of condensation polymers.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

R. Clary, C. Lee, W. Monroe IV, D. Vaughn, R. Ragheb, J. Erter III, D. Brown and D. Schiraldi, "A Green, One-Pot Route to the Biphenyldicarboxylic Acids: Useful Intermediates in Polymer Synthesis," International Journal of Organic Chemistry, Vol. 3 No. 2, 2013, pp. 143-147. doi: 10.4236/ijoc.2013.32016.

References

[1] C. K. Ober, J.-I. Jin and R. W. Lenz, “Liquid Crystal Polymers with Flexible Spacers in the Main Chain,” Advances in Polymer Science, Vol. 59, 1984, pp. 103-146. doi:10.1007/3-540-12818-2_8
[2] A. Ciferri, “Liquid Crystallinity in Polymers, Principles and Fundamental Properties,” VCH, New York, 1991.
[3] J. R. Greuel, T. E. Andrews, J. J. Wichman, J. D. Tessner and K. N. Wiegel, “Supramolecular Main-Chain Liquid Crystalline Polymers and Networks with Competitive Hydrogen Bonding: Networks and Linear Polymers Created from Trisand Bis-Functionalised Pyridyl Networking Agents,” Liquid Crystals, Vol. 37, No. 12, 2010, pp. 1515-1520. doi:10.1080/02678292.2010.531404
[4] Y. S. Hu, H. P. Wang, D. A. Schiraldi, A. Hiltner and E. Baer, “Oxygen-Transport Properties of Liquid-Crystalline Polyesters Based on 4,4'-Bibenzoic Acid,” Journal of Applied Polymer Science, Vol. 105, No. 1, 2007, pp. 30-37. doi:10.1002/app.26008
[5] H. Ma, D. M. Collard, D. A. Schiraldi, S. Kumar, “Structure and Dynamic Mechanical Properties of Poly(ethylene terephthalate-co-4, 4'-bibenzoate) Fibers,” Polymer, Vol. 48, No. 6, 2007, pp. 1651-1658.
[6] H. Ma, T. Uchida, D. M. Collard, D. A. Schiraldi and S. Kumar, “Crystal Structure and Composition of Poly(ethylene tereph-thalate-co-4,4‘-bibenzoate),” Macromolecules, Vol. 37, No. 20, 2004, pp. 7643-7648. doi:10.1021/ma0486905
[7] B. Min, S. Kumar, D. A. Schiraldi, M. R. Hibbs, H. Ma and D. M. Collard, “Sequence Analysis and Fiber Properties of a Blend of Poly(ethylene tereph-thalate) and Poly(ethylene terephthalate-co-4,4'-bibenzoate),” Journal of Applied Polymer Science, Vol. 93, No. 4, 2004, pp. 1793-1803. doi:10.1002/app.20638
[8] Y. S. Hu, R. Y. F. Liu, D. A. Schiraldi, A. Hiltner and E. Baer, “Oxygen Barrier Properties of Copolyesters Containing a Mesogenic Monomer,” Macromolecules, Vol. 37, No. 6, 2004, pp. 2136-2143.
[9] Y. S. Hu, R. Y. F. Liu, D. A. Schiraldi, A. Hiltner and E. Baer, “Solid-State Structure of Copolyesters Containing a Mesogenic Monomer,” Macromolecules, Vol. 37, No. 6, 2004, pp. 2128-2135. doi:10.1021/ma030439m
[10] R. Y. F. Liu, Y. S. Hu, M. R. Hibbs, D. M. Collard, D. A. Schiraldi, A. Hiltner and E. Baer, “Comparison of Statistical and Blocky Copolymers of Ethylene Terephthalate and Ethylene 4,4'-Bibenzoate Based on Thermal Behavior and Oxygen Transport Properties,” Journal of Polymer Science Part B: Polymer Physics, Vol. 41, No. 3, 2003, pp. 289-307. doi:10.1002/polb.10380
[11] Y. S. Hu, R. Y. F. Liu, M. Rogunova, D. A. Schiraldi, S. Nazarenko, A. Hiltner and E. Baer, “Oxygen-Barrier Properties of Cold-Crystallized and Melt-Crystallized Poly(ethylene terephthalate-co-4,4'-bibenzoate),” Journal of Polymer Science Part B: Polymer Physics, Vol. 40, No. 22, 2002, pp. 2489-2503. doi:10.1002/polb.10307
[12] N. Miyuara, T. Yanagi and A. Suzuki, “The PalladiumCatalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases,” Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, Vol. 11, No. 7, 1981, pp. 513-519. doi:10.1080/00397918108063618
[13] A. Suzuki, “Synthetic Studies via the Cross-Coupling Reaction of Organoboron Derivatives with Organic Halides,” Pure and Applied Chemistry, Vol. 63, No. 3, 1991, pp. 419-422. doi:10.1351/pac199163030419
[14] N. Miyaura and A. Suzuki, “Palladium-Catalyzed CrossCoupling Reactions of Organoboron Compounds,” Chemical Review, Vol. 95, No. 7, 1995, pp. 2457-2483. doi:10.1021/cr00039a007
[15] S. P. Stanforth, “Catalytic Cross-Coupling Reactions in Biaryl Synthesis,” Tetrahedron, Vol. 54, No. 3-4, 1998, pp. 263-303. doi:10.1016/S0040-4020(97)10233-2
[16] A. Suzuki, “Cross-Coupling Reactions of Organoboranes: An Easy Way to Construct C-C Bonds (Nobel Lecture),” Angewandte Chemie International Edition, Vol. 50, No. 30, 2011, pp. 6722-6737. http://onlinelibrary.wiley.com/doi/10.1002/anie.201101379/abstract
[17] J. Fu, B. Zhao, M. J. Sharp and V. Snieckus, “Ortho and Remote Metalation—Cross Coupling Strategies. Total Synthesis of the Naturally Occurring Fluorenone Dengibsinin and the Azafluoranthene Alkaloid Imeluteine,” Canadian Journal of Chemistry, Vol. 72, No. 1, 1994, pp. 227-236. doi:10.1139/v94-035
[18] B. Zhao and V. Snieckus, “Integrated Aromatic Metalation—Cross Coupling Methodologies. A Concise Synthesis of the Azafluoranthene Alkaloid Imeluteine,” Tetrahedron Letters, Vol. 32, No. 39, 1991, pp. 5277-5278. doi:10.1016/S0040-4039(00)92363-3
[19] X. Wang and V. Snieckus, “Synthetic Strategies Based on Aromatic Metalation—Cross Coupling Links. Regiospecific Synthesis of the Phenanthrene Natural Product Gymnopusin,” Tetrahedron Letters, Vol. 32, No. 37, 1991, pp. 4879-4882. doi:10.1016/S0040-4039(00)93485-3
[20] B. I. Alo, A. Kandil, P. A. Patil, M. J. Sharp, M. A. Siddiqui and V. Snieckus, “Sequential Directed Ortho Metalation-Boronic Acid Cross-Coupling Reactions. A General Regiospecific Route to Oxygenated Dibenzo[b,d]pyran-6ones Related to Ellagic Acid,” Journal of Organic Chemistry, Vol. 56, No. 12, 1991, pp. 3763-3768. doi:10.1021/jo00012a004
[21] S. C. Stinson, “Wanted: Process Chemists To Tackle Challenges,” Chemical and Engineering News, Vol. 77, No. 25, 1999, pp. 45-51. doi:10.1021/cen-v077n025.p045
[22] S. Haber and H. J. Kleiner, “Process for Cross-coupling of Aromatic Compounds,” German Patent No. 19.527.118, 1995.
[23] S. Haber, “Cross-coupling Reaction for Preparation of Multinuclear Aromatic Compounds,” German Patent No. 19.535.528, 1995.
[24] S. Haber and N. Egger, “Catalyst for Cross-coupling Reactions,” German Patent No. 19.620.023, 1996.
[25] T. I. Wallow and B. M. Novak, “In Aqua Synthesis of Water-Soluble Poly(p-phenylene) Derivatives,” Journal of the American Chemical Society, Vol. 113, No. 19, 1991, pp. 7411-7412. doi:10.1021/ja00019a042
[26] J. M. Tour and J. J. S. Lambda, “Synthesis of Planar Poly(p-phenylene) Derivatives for Maximization of Extended .pi.-Conjugation,” Journal of the American Chemical Society, Vol. 115, No. 11, 1993, pp. 4935-4936. doi:10.1021/ja00064a083
[27] A. R. Martin and Y. Yang, “Palladium-Catalyzed CrossCoupling Reactions of Organoboronic Acids with Organic Electrophiles,” Acta Chemica Scan-dinavica, Vol. 47, 1993, pp. 221-230. doi:10.3891/acta.chem.scand.47-0221
[28] B. Cornils, “Industrial Aqueous Biphasic Catalysis:? Status and Directions,” Organic Process R&D, Vol. 2, No. 2, 1998, pp. 121-127. doi:10.1021/op970057e
[29] B. Cornils and W. A. Herrmann, “Aqueous-Phase Organometallic Catalysis,” Wiley-VCH Publishers, Weinheim, 1998.
[30] R. T. Baker and W. Tumas, “Homogeneous Catalysis. Toward Greener Chemistry,” Science, Vol. 284, No. 5419, 1999, pp. 1477-1479. doi:10.1126/science.284.5419.1477
[31] M. N. Mang, J. L. Brewbaker, “Thermoplastic Polyesters Containing Biphenylene Linkages,” US Patent No. 5,138,022, 1992.
[32] “Dictionary of Organic Compounds,” 5th Edition, Vol. 5, Chapman and Hall, New York, 1982.

  
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