Microwave-Assisted Synthesis of 2-Aryl and 2,5-Diarylthiophene Derivatives via Suzuki-Miyaura Cross-Coupling Using Novel Palladium Complex as a Catalyst

References

• R. Shah and P. K. Verma, “Therapeutic Importance of Synthetic Thiophene,” Chemistry Central Journal 12, no. 1 (2018): 137–59.
   PubMedGoogle Scholar
• I. M. Fakhr, M. A. Radwan, S. El-Batran, O. M. Abd El-Salam, and S. M. El-Shenawy, “Synthesis and Pharmacological Evaluation of 2-Substituted Benzo[B]Thiophenes as Anti-Inflammatory and Analgesic Agents,” European Journal of Medicinal Chemistry 44, no. 4 (2009): 1718–25.
   PubMed Web of Science ®Google Scholar
• H.-J. Chen, W.-L. Wang, G.-F. Wang, L.-P. Shi, M. Gu, Y.-D. Ren, L.-F. Hou, P.-L. He, F.-H. Zhu, X.-G. Zhong, et al. “Rational Design and Synthesis of 2,2-Bisheterocycle Tandem Derivatives as Non-Nucleoside Hepatitis B Virus Inhibitors,” Chemmedchem 3, no. 9 (2008): 1316–21.
   PubMed Web of Science ®Google Scholar
• K. Elumalai, R. Raja, J. Karunakaran, A. Mohanakrishnan, and K. Murugesan, (“E)-2-(3-Oxo-3-Phenylprop-1-Enyl) Thiophene-3-Carbaldehyde,” IUCrData 3, no. 1 (2018): x180041.
   Google Scholar
• A. O. Abdelhamid, “Convenient Synthesis of Some New Pyrazolo[1,5‐a]Pyrimidine, Pyridine, Thieno[2,3‐b]Pyridine, and Isoxazolo[3,4‐d]Pyridazine Derivatives Containing Benzofuran Moiety,” Journal of Heterocyclic Chemistry 46, no. 4 (2009): 680–6.
   Web of Science ®Google Scholar
• C. Sharma, S. Yerande, R. Chavan, and A. V. Bhosale, “Synthesis of Thienopyrimidines and Their Antipsychotic Activity,” E-Journal of Chemistry 7, no. 2 (2010): 655–64.
   Google Scholar
• X. M. Wu, X. S. Wu, and J. Y. Xu, “Synthesis and Bio-Activity of 2-Alkyl-3H Imidazo [4, 5-b] Pyridines,” Journal of China Pharmaceutical University 27 (1996): 641–6.
   Google Scholar
• D. A. Burnett, M. A. Caplen, H. R. Davis, Jr., R. E. Burrier, and J. W. Clader, “2-Azetidinones as Inhibitors of Cholesterol Absorption,” Journal of Medicinal Chemistry 37, no. 12 (1994): 1733–6.
   PubMed Web of Science ®Google Scholar
• R. Fnkel, Lippincott’s Pharmacolog, 4th ed (India: Wolter Kluwer (I) Pvt. Ltd, 2010).
   Google Scholar
• M. Hranjec, I. Piantanida, M. Kralj, L. Suman, K. Pavelić, and G. Karminski-Zamola, “Novel Amidino-Substituted Thienyl- and Furylvinylbenzimidazole: Derivatives and Their Photochemical Conversion into Corresponding Diazacyclopenta[C]Fluorenes. Synthesis, Interactions with DNA and RNA, and Antitumor Evaluation. 4,” Journal of Medicinal Chemistry 51, no. 16 (2008): 4899–910.
   PubMed Web of Science ®Google Scholar
• A. Suzuki, “Cross-Coupling Reactions via Organoboranes,” Journal of Organometallic Chemistry 653, no. 1–2 (2002): 83–90.
   Web of Science ®Google Scholar
• G. Ding, L. Hao, H. Xu, L. Wang, J. Chen, T. Li, X. Tu, and Q. Zhang, “Atomically Dispersed Palladium Catalyses Suzuki–Miyaura Reactions under Phosphine-Free Conditions,” Communications Chemistry 3 (2020): 1–8. doi: 10.1038/s42004-020-0289-y
   Web of Science ®Google Scholar
• C. Len, “Catalysts for Suzuki–Miyaura Coupling Reaction,”Catalysts 10, no. 1 (2020): 50–2.
   Web of Science ®Google Scholar
• J. El-Maiss, T. Mohy El Dine, C.-S. Lu, I. Karamé, A. Kanj, K. Polychronopoulou, and J. Shaya, “Recent Advances in Metal-Catalyzed Alkyl–Boron (C (sp3))–C (sp2)) Suzuki-Miyaura Cross-Couplings,”Catalysts 10, no. 3 (2020): 296–302.
   Web of Science ®Google Scholar
• S. T. Laughlin and C. R. Bertozzi, “Metabolic Labeling of Glycans with Azido Sugars and Subsequent Glycan-Profiling and Visualization via Staudinger Ligation,”Nature Protocols 2, no. 11 (2007): 2930–44.
   PubMed Web of Science ®Google Scholar
• A. Y. Khormi, T. A. Farghaly, and M. R. Shaaban, “New Palladium (II)-Complex Based on Nitrogen Rich Ligand Efficient Precatalyst for C–C Cross-Coupling in Water under Microwaves Irradiation,” Journal of Inorganic and Organometallic Polymers and Materials 30, no. 12 (2020): 5133–15.
   Web of Science ®Google Scholar
• L. Botella and C. Nájera, “Convenient Oxime‐Carbapalladacycle‐Catalyzed Suzuki Cross‐Coupling of Aryl Chlorides in Water,” Angewandte Chemie International Edition 41, no. 1 (2002): 179–81.
   PubMed Web of Science ®Google Scholar
• S. M. Islam, P. Mondal, K. Tuhina, A. S. Roy, S. Mondal, and D. Hossain, “A Reusable Polymer-Anchored Palladium (II) Schiff Base Complex Catalyst for the Suzuki Cross-Coupling, Heck and Cyanation Reactions,” Journal of Inorganic and Organometallic Polymers and Materials 20, no. 2 (2010): 264–77.
   Web of Science ®Google Scholar
• E. Peris, “Smart N-Heterocyclic Carbene Ligands in Catalysis,”Chemical Reviews 118, no. 19 (2018): 9988–10031.
   PubMed Web of Science ®Google Scholar
• D. Kovala-Demertzi, N. Kourkoumelis, K. Derlat, J. Michalak, F. J. Andreadaki, and I. D. Kostas, “Thiosemicarbazone-Derivatised Palladium Nanoparticles as Efficient Catalyst for the Suzuki–Miyaura Cross-Coupling of Aryl Bromides with Phenylboronic Acid,” Inorganica Chimica Acta 361, no. 5 (2008): 1562–5.
   Web of Science ®Google Scholar
• P. C. B. Page, B. R. Buckley, S. D. Christie, M. Edgar, A. M. Poulton, M. R. Elsegood, and V. McKee, “A New Paradigm in N-Heterocyclic Carbenoid Ligands,” Organometallic Chemistry 690, no. 24–25 (2005): 6210–6.
   Web of Science ®Google Scholar
• G. N. Babu and S. Pal, “Mono- and Dinuclear Cyclopalladates as Catalysts for Suzuki–Miyaura Cross-Coupling Reactions in Predominantly Aqueous Media,” Tetrahedron Letters 58, no. 10 (2017): 1000–5.
   Web of Science ®Google Scholar
• A. Kumbhar, “Functionalized Nitrogen Ligands for Palladium Catalyzed Cross-Coupling Reactions (Part I),” Journal of Organometallic Chemistry 848 (2017): 22–88.
   Web of Science ®Google Scholar
• A. Kumbhar, “Functionalized Nitrogen Ligands (CN) for Palladium Catalyzed Cross-Coupling Reactions (Part II),” Journal of Organometallic Chemistry 881 (2019): 79–129.
   Web of Science ®Google Scholar
• X. Li, W. Zhang, L. Fu, and M. Guo, “Pd (CH3CN)2Cl2/Pipecolinic Acid as a Highly Efficient Catalytic System for Suzuki-Miyaura Cross-Coupling Reaction of Bromoaryl Carboxylic Acids in Water,”Catalysts 9, no. 1 (2019): 86.
   Web of Science ®Google Scholar
• A.-C. Tenchiu, I.-K. Ventouri, G. Ntasi, D. Palles, G. Kokotos, D. Kovala-Demertzi, and I. D. Kostas, “Synthesis of a Palladium Complex with a β-d-Glucopyranosyl-Thiosemicarbazone and Its Application in the Suzuki–Miyaura Coupling of Aryl Bromides with Phenylboronic Acid,” Inorganica Chimica Acta 435 (2015): 142–6.
   Google Scholar
• P. Lidström, J. Tierney, B. Wathey, and J. Westman, “Microwave Assisted Organic Synthesis—A Review,” Tetrahedron 57, no. 45 (2001): 9225–83.
   Web of Science ®Google Scholar
• C. O. Kappe, A. Stadler, and D. Dallinger, Microwaves in Organic and Medicinal Chemistry (Hoboken, NJ, USA: John Wiley & Sons, 2012). doi:10.1002/3527606556
   Google Scholar
• A. de la Hoz, A. Diaz-Ortiz, and A. Moreno, “Microwaves in Organic Synthesis. Thermal and Non-Thermal Microwave Effects,” Chemical Society Reviews 34, no. 2 (2005): 164–78.
   PubMed Web of Science ®Google Scholar
• A. de la Hoz, A. Díaz-Ortiz, and P. Prieto, “Microwave-Assisted Green Organic Synthesis,” in Alternative Energy Sources for Green Chemistry, 1–33 (UK: Royal Society of Chemistry, 2016).
   Google Scholar
• K. S. Salih and Y. Baqi, “Microwave-Assisted Palladium-Catalyzed Cross-Coupling Reactions: Generation of Carbon–Carbon Bond,” Catalysts 10, no. 1 (2019): 4–13.
   Web of Science ®Google Scholar
• A. Y. Khormi, T. A. Farghaly, and M. R. Shaaban, “Pyrimidyl Formamidine Palladium(II) Complex as a Nanocatalyst for Aqueous Suzuki-Miyaura Coupling,” Heliyon 5, no. 3 (2019): e01367.
   PubMed Web of Science ®Google Scholar
• K. M. Dawood, A. F. Darweesh, M. R. Shaaban, and A. M. Farag, “Microwave-Promoted Heck and Suzuki Coupling Reactions of New 3-(5-Bromobenzofuranyl)Pyrazole in Aqueous Media,” Arkivoc 2018, no. 5 (2018): 348–58.
   Google Scholar
• M. R. Shaaban, T. A. Farghaly, A. Y. Khormi, and A. M. Farag, “Recent Advances in Synthesis and Uses of Heterocycles-​Based Palladium(II) Complexes as Robust, Stable, and Low-​Cost Catalysts for Suzuki- Miyaura Crosscouplings,” Current Organic Chemistry 23, no. 15 (2019): 1601–62.
   Web of Science ®Google Scholar
• A. F. Darweesh, M. R. Shaaban, A. M. Farag, P. Metz, and K. M. Dawood, “Facile Access to Biaryls and 2-Acetyl-5-Arylbenzofurans via Suzuki Coupling in Water under Thermal and Microwave Conditions,” Synthesis 2010, no. 18 (2010): 3163–73.
   Google Scholar
• M. R. Shaaban, A. F. Darweesh, K. M. Dawood, and A. M. Farag, “Mizoroki-Heck Cross-Couplings of 2-Acetyl-5-Bromobenzofuran and Aryl Halides under Microwave Irradiation,” Arkivoc 2010, no. 10 (2010): 208–25.
   Google Scholar
• U. Holzwarth and N. Gibson, “The Scherrer Equation versus the 'Debye-Scherrer equation',” Nature Nanotechnology 6, no. 9 (2011): 534.
   PubMed Web of Science ®Google Scholar
• I. Hoffmann, B. Blumenröder, S. O. Neé Thumann, S. Dommer, and J. Schatz, “Suzuki Cross-Coupling in Aqueous Media,” Green Chemistry 17, no. 7 (2015): 3844–57.
   Web of Science ®Google Scholar
• M. Nowotny, U. Hanefeld, H. Koningsveld, and T. Maschmeyer, “Cyclopalladated Imine Catalysts in Heck Arylation: Search for the Catalytic Species,” Chemical Communications 19, no. 19 (2000): 1877–78.
   Google Scholar
• K. Yu, W. Sommer, J. M. Richardson, M. Weck, and C. W. Jones, “Evidence That SCS Pincer Pd(II) Complexes Are Only Precatalysts in Heck Catalysis and the Implications for Catalyst Recovery and Reuse,” Advanced Synthesis & Catalysis 347, no. 1 (2005): 161–71.
   Web of Science ®Google Scholar
• D. E. Bergbreiter, P. L. Osburn, and J. D. Frels, “Mechanistic Studies of SCS-Pd Complexes Used in Heck Catalysis,” Advanced Synthesis & Catalysis 347, no. 1 (2005): 172–84.
   Web of Science ®Google Scholar
• A. Kumar, G. K. Rao, S. Kumar, and A. K. Singh, “Formation and Role of Palladium Chalcogenide and Other Species in Suzuki–Miyaura and Heck C-C Coupling Reactions Catalyzed with Palladium(II) Complexes of Organochalcogen Ligands: Realities and Speculations,” Organometallics 33, no. 12 (2014): 2921–43.
   Web of Science ®Google Scholar
• A. Kumar, G. K. Rao, and A. K. Singh, “Organochalcogen Ligands and Their Palladium(II)Complexes: Synthesis to Catalytic Activity for Heck Coupling,” RSC Advances 2, no. 33 (2012): 12552–74.
   Web of Science ®Google Scholar
• N. T. S. Phan, M. V. D. Sluys, and C. W. Jones, “On the Nature of the Active Species in Palladium Catalyzed Mizoroki–Heck and Suzuki–Miyaura Couplings – Homo-Geneous or Heterogeneous Catalysis, A Critical Review,” Advanced Synthesis & Catalysis 348, no. 6 (2006): 609–79.
   Web of Science ®Google Scholar
• A. Kumar, G. K. Rao, F. Saleem, R. Kumar, and A. K. Singh, “Efficient Catalysis of Suzuki-Miyaura C-C Coupling Reactions with Palladium(II) Complexes of Partially Hydrolyzed Bisimine Ligands: A Process Important in Environment Context,” Journal of Hazardous Materials 269, (2014): 9–17.
   PubMed Web of Science ®Google Scholar
• J. T. Gupton, N. Telang, E. J. Banner, E. J. Kluball, K. E. Hall, K. L. Finzel, X. Jia, S. R. Bates, R. S. Welden, B. C. Giglio, et al. “The Application of (Z)-3-Aryl-3-Haloenoic Acids to the Synthesis of (Z)-5-Benzylidene-4-Arylpyrrol-2(5H)-Ones,” Tetrahedron 66, no. 47 (2010): 9113–122.
   PubMed Web of Science ®Google Scholar
• Y. Zhongsheng, C. Fuheng, “Synthesis of amide-​containing pyrimidines and their bioactivity”, Yingyong Huaxue 7 (1990): 54–57.
   Google Scholar
• M. L. Rao, D. Banerjee, and R. J. Dhanorkar, “Synthesis of Functionalized 2-Arylthiophenes with Triarylbismuths as Atom-Efficient Multicoupling Organometallic Nucleophiles under Palladium Catalysis,” Synlett 2011, no. 09 (2011): 1324–30.
   Google Scholar
• T. Li, Y. Yang, C. Cheng, A. K. Tiwari, K. Sodani, Y. Zhao, I. Abraham, and Z.-S. Chen, “Design, Synthesis and Biological Evaluation of N-Arylphenyl-2,2-Dichloroacetamide Analogues as Anti-Cancer Agents,” Bioorganic & Medicinal Chemistry Letters 22, no. 23 (2012): 7268–71.
   PubMed Web of Science ®Google Scholar
• H. Peng, Y.-Q. Chen, S.-L. Mao, Y.-X. Pi, Y. Chen, Z.-Y. Lian, T. Meng, S.-H. Liu, and G.-A. Yu, “A General Catalyst for Suzuki-Miyaura and Sonogashira Reactions of Aryl and Heteroaryl Chlorides in Water,” Organic & Biomolecular Chemistry 12, no. 35 (2014): 6944–52.
   PubMed Web of Science ®Google Scholar
• D. Urselmann, D. Antovic, and T. J. Müller, “Pseudo Five-Component Synthesis of 2,5-Di(hetero)Arylthiophenes via a One-Pot Sonogashira-Glaser Cyclization Sequence,” Beilstein Journal of Organic Chemistry 7 (2011): 1499–1503.
   PubMed Web of Science ®Google Scholar
• J. Tang and X. Zhao, “Synthesis of 2,5-Disubstituted Thiophenes via Metal-Free Sulfur Heterocyclization of 1,3-Diynes with Sodium Hydrosulfide,” RSC Advances 2, no. 13 (2012): 5488–490.
   Web of Science ®Google Scholar