Copper-Free, Pd(OAc)₂ and Ruphos Catalyzed, C_sp²-C_sp Bond Formation of Tautomerizable Quinolinones

Reference

• R. Chinchilla, and C. Najera, “Recent Advances in Sonogashira Reactions,” Chemical Society Reviews 40, no. 10 (2011): 5084–121.
   PubMed Web of Science ®Google Scholar
• R. Chinchilla, and C. Najera, “The Sonogashira Reaction: A Booming Methodology in Synthesis Organic Chemcistry,” Chemical Reviews 107, no. 3 (2007): 874–922.
   PubMed Web of Science ®Google Scholar
• H. Doucet, and J. C. Hierso, “Palladium-Based Catalytic System for the Synthesis of Conjugated Enynes by Sonogashira Reactions and Related Alkynylation,” Angewandte Chemie International Edition 46, no. 6 (2007): 834–71.
   PubMed Web of Science ®Google Scholar
• H. Plenio, “Catalysts for the Sonogashira Coupling-the Crownless again Shall be King,” Angewandte Chemie (International ed. in English) 47, no. 37 (2008): 6954–6.
   PubMed Web of Science ®Google Scholar
• N. M. Jenny, M. Mayor, and T. R. Eaton, “Phenyl-Acetylene Bond Assembly: A Powerful Tool for the Construction of Nanoscale Architectures,” European Journal of Organic Chemistry 2011, no. 26 (2011): 4965–83.
   Web of Science ®Google Scholar
• N. E. Leadbeater, “Cross Coupling: When is Free Really Free?,” Nature Chemistry 2, no. 12 (2010): 1007–9.
   PubMed Web of Science ®Google Scholar
• A. Sharma, D. Vachhani, and E. V. der Eycken, “Direct Heteroarylation of Tautomerizable Heterocycles into Unsymmetrical and Symmetrical Biheterocycles via Pd/Cu-catalyzed Phosphonium Coupling,” Organic Letters 14, no. 7 (2012): 1854–7.
   PubMed Web of Science ®Google Scholar
• V. P. Mehta, S. G. Modha, and E. V. der Eycken, “Microwave-Assisted Palladium-Catalyzed Phosphonium Coupling of 2(1H)-Pyrazinones,” The Journal of Organic Chemistry 75, no. 3 (2010): 976–9.
   PubMed Web of Science ®Google Scholar
• C. Shi, and C. C. Aldrich, “Efficient Pd-catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C-OH Bond Activation using PyBrOP,” Organic Letters 12, no. 10 (2010): 2286–9.
   PubMed Web of Science ®Google Scholar
• F. A. Kang, Z. Sui, and W. V. Murray, “Pd-Catalyzed Direct Arylation of Tautomerizable Heterocycles with Aryl Boronic Acids via C-OH Bond Activation using Phosphonium Salts,” Journal of the American Chemical Society 130, no. 34 (2008): 11300–2.
   PubMed Web of Science ®Google Scholar
• F. A. Kang, J. Kodah, Q. Guan, X. Li, and W. V. Murray, “Efficient Conversion of Biginelli 3,4-Dihydropyrimidin-2(1H)-one to Pyrimidines via PyBroP-Mediated Coupling,” The Journal of Organic Chemistry 70, no. 5 (2005): 1957–60.
   PubMed Web of Science ®Google Scholar
• F. A. Kang, Z. Sui, and W. V. Murray, “Phosphonium Coupling in the Direct Bond Formation of Tautomerizable Heterocycles via C-OH Bond Activation,” European Journal of Organic Chemistry 2009, no. 4 (2009): 461–79.
   Web of Science ®Google Scholar
• F. A. Kang, J. C. Lanter, C. Cai, Z. Sui, and W. V. Murray, “Direct Dehydrative Cross-Coupling of Tautomerizable Heterocycles with Alkynes via Pd/Cu-catalyzed Phosphonium Coupling,” Chemical Communications (Cambridge, England) 46, no. 8 (2010): 1347–9.
   PubMed Web of Science ®Google Scholar
• Z. K. Wan, S. Wacharasindhu, C. G. Levins, M. Lin, K. Tabei, and T. S. Mansour, “The Scope and Mechanism of Phosphonium-mediated S(N)Ar Reactions in Heterocyclic Amides and Ureas,” The Journal of Organic Chemistry 72, no. 26 (2007): 10194–210.
   PubMed Web of Science ®Google Scholar
• Z. K. Wan, S. Wacharasindhu, E. Binnu, and T. S. Mansour, “An Efficient Direct Amination of Cyclic Amides and Cyclic Ureas,” Organic Letters 8, no. 11 (2006): 2425–8.
   PubMed Web of Science ®Google Scholar
• N. T. Patil, F. Nawaz Khan, and Y. Yamamoto, “Microwave-Enhanced Pd(0)/Acetic Acid Catalysed Allylation Reactions of C,N, and O-Pronucleophiles with Alkynes,” Tetrahedron Letters 45, no. 46 (2004): 8497–9.
   Web of Science ®Google Scholar
• Y. Isogai, F. Nawaz Khan, and N. Asao, “CuX2-Mediated [4 + 2] Benzannulation as a New Synthetic Tool for Stereoselective Construction of Haloaromatic Compounds,” Tetrahedron 65, no. 14 (2009): 9575–82.
   Google Scholar
• K. Prabakaran, F. R. N. Khan, J. S. Jin, E. D. Jeong, and P. Manivel, “Facile Synthesis of 3-Aryl-1-((4-Aryl-1,2,3-Selenadiazol-5-yl)Sulfanyl)Isoquinolines,” Chemical Papers 65, no. 6 (2011): 883–9.
   Web of Science ®Google Scholar
• K. Prabakaran, F. Nawaz Khan, and J. S. Jin, “Än Efficient Copper-Free Pd(OAc)2/Ruphos-Catalysed Sonogashira Coupling of 1-Chloroisoquinolines in the Formation of 1-Alkynyl-3-Substituted Isoquinolines,” Tetrahedron Letters 52, no. 20 (2011): 2566–70.
   Web of Science ®Google Scholar
• R. Subashini, and F. R. N. Khan, “Solvent-Free Synthesis and Antibacterial Studies of Some Quinolines,” Monatshefte Für Chemie - Chemical Monthly 143, no. 3 (2012): 485–9.
   Google Scholar
• S. M. Roopan, F. R. N. Khan, and B. K. Mandal, “Fe-Nano Particles Mediated C-N Bond-Forming Reaction: Regioselective Synthesis of 3-[(2-Chloroquinolin-3-yl)Methyl]Pyrimidin-4(3H)Ones,” Tetrahedron Letters 51, no. 17 (2010): 2309–11.
   Web of Science ®Google Scholar
• S. M. Roopan, T. Maiyalagan, and F. Nawaz Khan, “Solvent-Free Synthesis of Some Quinolin-4(3H)-Ones Derivatives,” Canadian Journal of Chemistry 86, no. 11 (2008): 1019–25. no.
   Google Scholar
• S. M. Roopan, and F. R. Nawaz Khan, “SnO2 Nanoparticles Mediated Nontraditional Synthesis of Biologically Active 9-Chloro-6,13-Dihydro-7-Phenyl-5H-Indolo[3,2-c]-Acridine Derivatives,” Medicinal Chemistry Research 20, no. 6 (2011): 732–7.
   Web of Science ®Google Scholar
• V. Krishnakumar, F. R. Nawaz Khan, B. K. Mandal, and E. D. Jeong, “Water Mediated Catalyst-Free Efficient Domino Synthesis of 9-(Quinolin-2(1H)-One)-Xanthene-1,8(5H,9H)-Diones Using Parallel Synthesizer,” Tetrahedron Letters 55, no. 27 (2014): 3717–20.
   Web of Science ®Google Scholar
• P. Manivel, K. Prabakaran, V. Krishnakumar, F. Nawaz Khan, and T. Maiyalagan, “Thiourea-Mediated Regioselective Synthesis of Symmetrical and Unsymmetrical Diversified Thioethers,” Industrial & Engineering Chemistry Research 53, no. 19 (2014): 7866–70.
   Web of Science ®Google Scholar
• M. Gund, F. R. N. Khan, A. Khanna, and V. Krishnakumar, “Nicotinic Acid Conjugates of Nonsteroidal anti-Inflammatory Drugs (NSAID's) and their Anti-Inflammatory Properties,” European Journal of Pharmaceutical Sciences: Official Journal of the European Federation for Pharmaceutical Sciences 49, no. 2 (2013): 227–32.
   PubMed Web of Science ®Google Scholar
• K. R. Ethiraj, A. Jesil Mathew, and F. N. Khan, “Synthesis of Methoxy-Substituted Chalcones and in Vitro Evaluation of Their Anticancer Potential,” Chemical Biology & Drug Design 82, no. 6 (2013): 732–42.
   PubMed Web of Science ®Google Scholar
• K. R. Ethiraj, J. M. Aranjani, and F. N. Khan, “Potential Cytotoxic and Apoptosis Inducing Agents: Synthesis and Evaluation of Methoxy-Substituted Chalcones against Human Lung and Cervical Cancers,” Medicinal Chemistry Research 22, no. 11 (2013): 5408–17.
   Web of Science ®Google Scholar
• S. Syed Tajudeen, and F. Nawaz Khan, “Synthesis of Some 3-Substituted Isochromen-1-Ones,” Synthetic Communications 37, no. 20 (2007): 3649–56.
   Google Scholar
• Yadavalli Suneel Kumar, C. Dasaradhan, Kamalakannan Prabakaran, Fazlur-Rahman Nawaz Khan, Euh Duck Jeong, Eun Hyuk Chung, and Hyun Gyu Kim Hyun Gyu Kim, “Ä convenient and Efficient C-OH Bond Activation, PdCl2(PPh3)2 Catalysed, C-C Bond Formation of Tautomerizable Quinolines with the Aid of BOP Reagent and Boronic Acids,” RSC Advances 4, no. 76 (2014): 40259–68.
   Web of Science ®Google Scholar