Efficient and Solvent-Free Oxidation Coupling of Amines to Imines Using Persulfate as Oxidant with Ultrasound Assistance

References

• S. Kobayashi, Y. Mori, J. S. Fossey, and M. M. Salter, “Catalytic Enantioselective Formation of C-C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update,” Chemical Reviews 111, no. 4 (2011): 2626–704.
   PubMed Web of Science ®Google Scholar
• J. Gawronski, N. Wascinska, and J. Gajewy, “Recent Progress in Lewis Base Activation and Control of Stereoselectivity in the Additions of Trimethylsilyl Nucleophiles,” Chemical Reviews 108, no. 12 (2008): 5227–52.
   PubMed Web of Science ®Google Scholar
• H. Naeimi, F. Salimi, and K. Rabiei, “Mild and Convenient One Pot Synthesis of Schiff Bases in the Presence of P2O5/Al2O3 as New Catalyst under Solvent-Free Conditions,” Journal of Molecular Catalysis A: Chemical. 260, no. 1-2 (2006): 100–4.
   Google Scholar
• M. Largeron, “Protocols for the Catalytic Oxidation of Primary Amines to Imines,” European Journal of Organic Chemistry 2013, no. 24 (2013): 5225–35.
   Web of Science ®Google Scholar
• P. Choudhary, A. Sen, A. Kumar, S. Dhingra, C. M. Nagaraja, and V. Krishnan, “Sulfonic Acid Functionalized Graphitic Carbon Nitride as Solid Acid–Base Bifunctional Catalyst for Knoevenagel Condensation and Multicomponent Tandem Reactions,” Materials Chemistry Frontiers 5, no. 16 (2021): 6265–8.
   Web of Science ®Google Scholar
• H. Sun, F. Z. Su, J. Ni, Y. Cao, H. Y. He, and K. N. Fan, “Gold Supported on Hydroxyapatite as a Versatile Multifunctional Catalyst for the Direct Tandem Synthesis of Imines and Oximes,” Angewandte Chemie (International ed. in English) 48, no. 24 (2009): 4390–3.
   PubMed Web of Science ®Google Scholar
• Ilkay Gumus, Yaşar Karataş, and Mehmet Gülcan, “Silver Nanoparticles Stabilized by a Metal–Organic Framework (MIL-101(Cr)) as an Efficient Catalyst for Imine Production from the Dehydrogenative Coupling of Alcohols and Amines,” Catalysis Science & Technology 10, no. 15 (2020): 4990–9.
   Web of Science ®Google Scholar
• F. Bottaro, and R. Madsen, “In Situ Generated Cobalt Catalyst for the Dehydrogenative Coupling of Alcohols and Amines into Imines,” Chemcatchem. 11, no. 11 (2019): 2707–12.
   Web of Science ®Google Scholar
• S. Wu, H. Zhang, Q. Cao, Q. Zhao, and W. Fang, “Efficient Imine Synthesis via Oxidative Coupling of Alcohols with Amines in an Air Atmosphere Using a Mesoporous Manganese–Zirconium Solid Solution Catalyst,” Catalysis Science & Technology 11, no. 3 (2021): 810–22.
   Web of Science ®Google Scholar
• Gaoxi Jiang, Jian Chen, Jie-Sheng Huang, and Chi-Ming Che, “Highly Efficient Oxidation of Amines to Imines by Singlet Oxygen and Its Application in Ugi-Type Reactions,” Organic Letters 11, no. 20 (2009): 4568–71.
   PubMed Web of Science ®Google Scholar
• D. Liu, C. Zhang, N. Han, M. Du, X. Zhang, P. Zhao, and P. Yang, “Progress in Oxidative Coupling of Amines to Imines,” Chinese Journal of Organic Chemistry 38, no. 6 (2018): 1350–63.
   Web of Science ®Google Scholar
• J. D. Sitter, and A. K. Vannucci, “Photocatalytic Oxidative Coupling of Arylamines for the Synthesis of Azoaromatics and the Role of O2 in the Mechanism,” Journal of the American Chemical Society 143, no. 7 (2021): 2938–43.
   PubMed Web of Science ®Google Scholar
• A. J. Bailey, and B. R. James, “Catalysed Aerobic Dehydrogenation of Amines and an X-Ray Crystal Structure of a Bis(Benzylamine) Ruthenium(II) Porphyrin Species,” Chemical Communications 20, no. 20 (1996): 2343–4.
   Google Scholar
• B. Zhu, and R. J. Angelici, “Non-Nanogold Catalyzed Aerobic Oxidation of Secondary Amines to Imines,” Cheminform 38, no. 41 (2007): 2157–9.
   Google Scholar
• Lianyue Wang, Bo Chen, Lanhui Ren, Hengyun Zhang, Ying Lü, and Shuang Gao, “Vanadium Catalyzed Direct Synthesis of Imines from Amines or Alcohols and Amines by an Aerobic Oxidative Reaction under Mild Conditions,” Chinese Journal of Catalysis. 36, no. 1 (2015): 19–23.
   Web of Science ®Google Scholar
• D. Dissanayake, L. A. Achola, P. Kerns, D. Rathnayake, J. He, J. Macharia, and S. L. Suib, “Aerobic Oxidative Coupling of Amines to Imines by Mesoporous Copper Aluminum Mixed Metal Oxides via Generation of Reactive Oxygen Species (ROS),” Applied Catalysis B: Environmental. 249, (2019): 32–41.
   Web of Science ®Google Scholar
• X. Huang, G. Lu, K. Zhang, J. Liu, H. Zhang, Z. Guo, and J. Tao, “Selective Synthesis of Imines by Direct Oxidative Coupling of Amines on Cu-Doped CeO2 Catalysts,” Applied Surface Science. 514, (2020): 145948.
   Web of Science ®Google Scholar
• E. Zhang, H. Tian, S. Xu, X. Yu, and Q. Xu, “Iron-Catalyzed Direct Synthesis of Imines from Amines or Alcohols and Amines via Aerobic Oxidative Reactions under Air,”Organic Letters 15, no. 11 (2013): 2704–7.
   PubMed Web of Science ®Google Scholar
• S. Juntrapirom, S. Anuchai, O. Thongsook, S. Pornsuwan, P. Meepowpan, P. Thavornyutikarn, S. Phanichphant, D. Tantraviwat, and B. Inceesungvorn, “Photocatalytic Activity Enhancement of g-C3N4/BiOBr in Selective Transformation of Primary Amines to Imines and Its Reaction Mechanism,” Chemical Engineering Journal and the Biochemical Engineering Journal. 394, (2020): 124934.
   Google Scholar
• L.-H. Meng, X.-P. Tan, L. Chen, S. Shen, J.-K. Guo, C.-T. Au, and S.-F. Yin, “Fabrication of Mo2C-QDs/C/Bi2MoO6 Composite as Efficient Photocatalyst for Aerobic Oxidation of Amines to Imines,” Applied Surface Science. 541, (2021): 148476.
   Web of Science ®Google Scholar
• A. Khampuanbut, S. Santalelat, A. Pankiew, D. Channei, S. Pornsuwan, K. Faungnawakij, S. Phanichphant, and B. Inceesungvorn, “Visible-Light-Driven WO3/BiOBr Heterojunction Photocatalysts for Oxidative Coupling of Amines to Imines: Energy Band Alignment and Mechanistic Insight,” Journal of Colloid and Interface Science 560, (2020): 213–24.
   PubMed Web of Science ®Google Scholar
• X. Yang, T. Huang, S. Gao, and R. Cao, “Boosting Photocatalytic Oxidative Coupling of Amines by a Ru-Complex-Sensitized Metal-Organic Framework,” Journal of Catalysis. 378, (2019): 248–55.
   Web of Science ®Google Scholar
• J. P. Byrne, and M. Albrecht, “Anion-Cation Synergistic Metal-Free Catalytic Oxidative Homocoupling of Benzylamines by Triazolium Iodide Salts,” Organic & Biomolecular Chemistry 18, no. 37 (2020): 7379–87.
   PubMed Web of Science ®Google Scholar
• H. Wei, Y. Ma, J. Luo, K.-H. Wu, W. Xie, G. Wen, C.-L. Chiang, W. Yan, S. Perathoner, G. Centi, et al. “Reation of N-C = O Active Groups on N-Doped CNT as an Efficient CarboCatalyst for Solvent-Free Aerobic Coupling of Benzylamine,” Carbon 170, (2020): 338–46.
   Web of Science ®Google Scholar
• P. Choudhary, A. Bahuguna, A. Kumar, S. S. Dhankhar, C. M. Nagaraja, and V. Krishnan, “Oxidized Graphitic Carbon Nitride as a Sustainable Metal-Free Catalyst for Hydrogen Transfer Reactions under Mild Conditions,” Green Chemistry 22, no. 15 (2020): 5084–95.
   Web of Science ®Google Scholar
• Kuniaki Marui, Akihiro Nomoto, Michio Ueshima, and Akiya Ogawa, “Eco-Friendly Copper Sulfate-Catalyzed Oxidation of Amines to Imines by Hydrogen Peroxide in Water,” Tetrahedron Letters. 56, no. 10 (2015): 1200–2.
   Web of Science ®Google Scholar
• Guobiao Chu, and Chunbao Li, “Convenient and Clean Synthesis of Imines from Primary Benzylamines,” Organic & Biomolecular Chemistry 8, no. 20 (2010): 4716–9.
   PubMed Web of Science ®Google Scholar
• X.-F. Wu, A. Petrosyan, T. V. Ghochikyan, A. S. Saghyan, and P. Langer, “Metal-Free Oxidation of Benzyl Amines to Imines,” Tetrahedron Letters. 54, no. 24 (2013): 3158–9.
   Web of Science ®Google Scholar
• G. F. P. De Souza, T. W. von Zuben, and A. G. Salles, “On Water” Metal-Catalyst-Free Oxidative Coupling–Amidation of Amines to Access Imines and Amides,” ACS Sustainable Chemistry & Engineering 5, no. 9 (2017): 8439–46.
   Web of Science ®Google Scholar
• M. Brienza, and I. Katsoyiannis, “Sulfate Radical Technologies as TertiaryTreatment for the Removal of Emerging Contaminants from Wastewater,” Sustainability 9, no. 9 (2017): 1604–22.
   Web of Science ®Google Scholar
• J. Wang, X. Zhang, X. Zhou, M. G. Waigi, F. O. Gudda, C. Zhang, and W. Ling, “Promoted Oxidation of Polycyclic Aromatic Hydrocarbons in Soils by Dual Persulfate/Calcium Peroxide System,” The Science of the Total Environment 758, (2021): 143680.
   PubMed Web of Science ®Google Scholar
• G. Chen, Y. Yu, L. Liang, X. Duan, R. Li, X. Lu, B. Yan, N. Li, and S. Wang, “Remediation of Antibiotic Wastewater by Coupled Photocatalytic and Persulfate Oxidation System: A Critical Review,” Journal of Hazardous Materials 408, (2021): 124461.
   PubMed Web of Science ®Google Scholar
• S. Mandal, T. Bera, G. Dubey, J. Saha, and J. K. Laha, “Uses of K2S2O8 in Metal-Catalyzed and Metal-Free Oxidative Transformations,”ACS Catalysis 8, no. 6 (2018): 5085–144.
   Web of Science ®Google Scholar
• F. Minisci, A. Citterio, and C. Giordano, “Electron-Transfer Processes: peroxydisulfate, a Useful and Versatile Reagent in Organic Chemistry,”Accounts of Chemical Research 16, no. 1 (1983): 27–32.
   Web of Science ®Google Scholar
• W. P. Fagan, J. Zhao, F. A. Villamena, J. L. Zweier, and L. K. Weavers, “Synergistic, Aqueous PAH Degradation by Ultrasonically-Activated Persulfate Depends on Bulk Temperature and Physicochemical Parameters,” Ultrasonics Sonochemistry 67, (2020): 105172.
   PubMed Web of Science ®Google Scholar
• J. M. Costa, and A. F. Almeida Neto, “Ultrasound-Assisted Electrodeposition and Synthesis of Alloys and Composite Materials: A Review,” Ultrasonics Sonochemistry 68, (2020): 105193.
   PubMed Web of Science ®Google Scholar
• G. Liu, J. Qian, J. Hua, F. Cai, X. Li, and L. Liu, “An Economical Synthesis of Substituted Quinoline-2-Carboxylates through the Potassium Persulfate-Mediated Cross-Dehydrogenative Coupling of N-Aryl Glycine Derivatives with Olefins,” Organic & Biomolecular Chemistry 14, no. 3 (2016): 1147–52.
   PubMed Web of Science ®Google Scholar
• C. Zhang, P. Zhao, Z. Zhang, J. Zhang, P. Yang, P. Gao, J. Gao, and D. Liu, “Co–N–C Supported on SiO2: A Facile, Efficient Catalyst for Aerobic Oxidation of Amines to Imines,” RSC Advances. 7, no. 75 (2017): 47366–72.
   Web of Science ®Google Scholar
• S. L. Khursan, D. G. Semes’ko, and R. L. Safiullin, “Quantum-Chemical Modeling of the Detachment of Hydrogen Atoms by the Sulfate Radical Anion,” Russian Journal of Physical Chemistry 80, no. 3 (2006): 366–71.
   Web of Science ®Google Scholar
• G. P. Anipsitakis, D. D. Dionysiou, and M. A. Gonzalez, “Cobalt-Mediated Activation of Peroxymonosulfate and Sulfate Radical Attack on Phenolic Compounds. Implications of Chloride Ions,” Environmental Science & Technology 40, no. 3 (2006): 1000–7.
   PubMed Web of Science ®Google Scholar