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Abstract
Generally, several methods for the construction of biphenyls, including Stille coupling, Gomberg-Bachmann reaction, Ullmann reaction and Suzuki-Miyaura cross-coupling are reported. In present research, considering the particularities of these methods and the characteristics of the target compounds by Suzuki-Miyaura cross-coupling reaction. To investigate the optimal conditions, a model reaction was performed using 1-bromo-4-iodobenzene and phenyl boronic acid under different conditions. The products were characterized by FT-IR, mass, 1H NMR and 13C NMR spectroscopy.
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References
- N. Miyaura and S.L. Buchwald, Cross-Coupling Reactions: A Practical Guide, Springer (2010).
- K.C. Nicolaou, P.G. Bulger and D. Sarlah, Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis, Angew. Chem. Int. Ed., 44, 4442 (2005); https://doi.org/10.1002/anie.200500368
- C. Torborg and M. Beller, Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries, Adv. Synth. Catal., 351, 3027 (2009); https://doi.org/10.1002/adsc.200900587
- S. Huo, R. Mroz and J. Carroll, Negishi Coupling in the Synthesis of Advanced Electronic, Optical, Electrochemical and Magnetic Materials, Org. Chem. Front., 2, 416 (2015); https://doi.org/10.1039/C4QO00322E
- K. Sonogashira, Y. Tohda and N. Hagihara, A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes and Bromopyridines, Tetrahedron Lett., 16, 4467 (1975); https://doi.org/10.1016/S0040-4039(00)91094-3
- R.F. Heck, Acylation, Methylation, and Carboxyalkylation of Olefins by Group VIII Metal Derivatives, J. Am. Chem. Soc., 90, 5518 (1968); https://doi.org/10.1021/ja01022a034
- B. Cornils and W.A. Herrmann, Aqueous-Phase Organometallic Catalysis: Concepts and Applications; John Wiley & Sons (2004).
- U.M. Lindstrom, Organic Reactions in Water: Principles, Strategies and Applications; John Wiley & Sons (2008).
- C.-J. Li, Organic Reactions in Aqueous Media with a Focus on Carbon-Carbon Bond Formations: A Decade Update, Chem. Rev., 105, 3095 (2005); https://doi.org/10.1021/cr030009u
- C.-J. Li and T.-H. Chan, Comprehensive Organic Reactions in Aqueous Media; John Wiley & Sons (2007).
- N.E. Leadbeater and M. Marco, Ligand-Free Palladium Catalysis of the Suzuki Reaction in Water Using Microwave Heating, Org. Lett., 4, 2973 (2002); https://doi.org/10.1021/ol0263907
- T.E. Jacks, D.T. Belmont, C.A. Briggs, N.M. Horne, G.D. Kanter, G.L. Karrick, J.J. Krikke, R.J. McCabe, J.G. Mustakis, T.N. Nanninga, G.S. Risedorph, R.E. Seamans, R. Skeean, D.D. Winkle and T.M. Zennie, Development of a Scalable Process for CI-1034, an Endothelin Antagonist, Org. Process Res. Dev., 8, 201 (2004); https://doi.org/10.1021/op034104g
- P. Vicini, A. Geronikaki, K. Anastasia, M. Incerti and F. Zani, Synthesis and Antimicrobial Activity of Novel 2-thiazolylimino-5-arylidene-4-thiazolidinones, Bioorg. Med. Chem., 14, 3859 (2006); https://doi.org/10.1016/j.bmc.2006.01.043
- Y. Yamaguchi, I. Katsuyama, K. Funabiki, M. Matsui and K. Shibata, A New Expedient Route to 2,6-Diaryl-3-cyano-4-(trifluoromethyl)-pyridines, J. Heterocycl. Chem., 35, 805 (1998); https://doi.org/10.1002/jhet.5570350405
- National Committee for Clinical and Laboratory Standards, Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically Approved Standard, Fourth ed. NCCLS, Villanova, Italy, Document M 100-S7. S100-S157 (1997).
- D.H. Isenberg, Essential Procedure for Clinical Microbiology, American Society for Microbiology, Washington (1998).
References
N. Miyaura and S.L. Buchwald, Cross-Coupling Reactions: A Practical Guide, Springer (2010).
K.C. Nicolaou, P.G. Bulger and D. Sarlah, Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis, Angew. Chem. Int. Ed., 44, 4442 (2005); https://doi.org/10.1002/anie.200500368
C. Torborg and M. Beller, Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries, Adv. Synth. Catal., 351, 3027 (2009); https://doi.org/10.1002/adsc.200900587
S. Huo, R. Mroz and J. Carroll, Negishi Coupling in the Synthesis of Advanced Electronic, Optical, Electrochemical and Magnetic Materials, Org. Chem. Front., 2, 416 (2015); https://doi.org/10.1039/C4QO00322E
K. Sonogashira, Y. Tohda and N. Hagihara, A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes and Bromopyridines, Tetrahedron Lett., 16, 4467 (1975); https://doi.org/10.1016/S0040-4039(00)91094-3
R.F. Heck, Acylation, Methylation, and Carboxyalkylation of Olefins by Group VIII Metal Derivatives, J. Am. Chem. Soc., 90, 5518 (1968); https://doi.org/10.1021/ja01022a034
B. Cornils and W.A. Herrmann, Aqueous-Phase Organometallic Catalysis: Concepts and Applications; John Wiley & Sons (2004).
U.M. Lindstrom, Organic Reactions in Water: Principles, Strategies and Applications; John Wiley & Sons (2008).
C.-J. Li, Organic Reactions in Aqueous Media with a Focus on Carbon-Carbon Bond Formations: A Decade Update, Chem. Rev., 105, 3095 (2005); https://doi.org/10.1021/cr030009u
C.-J. Li and T.-H. Chan, Comprehensive Organic Reactions in Aqueous Media; John Wiley & Sons (2007).
N.E. Leadbeater and M. Marco, Ligand-Free Palladium Catalysis of the Suzuki Reaction in Water Using Microwave Heating, Org. Lett., 4, 2973 (2002); https://doi.org/10.1021/ol0263907
T.E. Jacks, D.T. Belmont, C.A. Briggs, N.M. Horne, G.D. Kanter, G.L. Karrick, J.J. Krikke, R.J. McCabe, J.G. Mustakis, T.N. Nanninga, G.S. Risedorph, R.E. Seamans, R. Skeean, D.D. Winkle and T.M. Zennie, Development of a Scalable Process for CI-1034, an Endothelin Antagonist, Org. Process Res. Dev., 8, 201 (2004); https://doi.org/10.1021/op034104g
P. Vicini, A. Geronikaki, K. Anastasia, M. Incerti and F. Zani, Synthesis and Antimicrobial Activity of Novel 2-thiazolylimino-5-arylidene-4-thiazolidinones, Bioorg. Med. Chem., 14, 3859 (2006); https://doi.org/10.1016/j.bmc.2006.01.043
Y. Yamaguchi, I. Katsuyama, K. Funabiki, M. Matsui and K. Shibata, A New Expedient Route to 2,6-Diaryl-3-cyano-4-(trifluoromethyl)-pyridines, J. Heterocycl. Chem., 35, 805 (1998); https://doi.org/10.1002/jhet.5570350405
National Committee for Clinical and Laboratory Standards, Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically Approved Standard, Fourth ed. NCCLS, Villanova, Italy, Document M 100-S7. S100-S157 (1997).
D.H. Isenberg, Essential Procedure for Clinical Microbiology, American Society for Microbiology, Washington (1998).