Humic acid-catalyzed efficient synthesis of α-aminonitriles in water using potassium hexacyanoferrate (II) as a cyanide source

References

• Enders, D.; Shilvock, J. P. Some Recent Applications of α-Amino Nitrile Chemistry. Chem. Soc. Rev. 2000, 29, 359–373. DOI: 10.1039/a908290e.
   Web of Science ®Google Scholar
• Kouznetsov, V. V.; Hernandez, J. G. Nanostructured Silicate Catalysts for Environmentally Benign Strecker-Type Reactions: Status Quo and Quo Vadis. RSC Adv. 2022, 12, 20807–20828. DOI: 10.1039/d2ra03102g.
   PubMed Web of Science ®Google Scholar
• Maleki, A.; Azadegan, S.; Rahimi, J. Gallic Acid Grafted to Amine-Functionalized Magnetic Nanoparticles as a Proficient Catalyst for Environmentally Friendly Synthesis of α-Aminonitriles. Appl. Organometal. Chem. 2019, 33, e4810. DOI: 10.1002/aoc.4810.
   Web of Science ®Google Scholar
• Wagner, A.; Ofial, A. R. Potassium Thiocyanate as Source of Cyanide for the Oxidative α-Cyanation of Tertiary Amines. J. Org. Chem. 2015, 80, 2848–2854. DOI: 10.1021/jo502846c.
   PubMed Web of Science ®Google Scholar
• Echevarria, I.; Vaquero, M.; Quesada, R.; Espino, G. Synthesis of α-Amino Nitriles through One-Pot Selective Ru-Photocatalyzed Oxidative Cyanation of Amines. Inorg. Chem. Front. 2020, 7, 3092–3105. DOI: 10.1039/D0QI00580K.
   Web of Science ®Google Scholar
• Wang, J.; Liu, X.; Feng, X. Asymmetric Strecker Reactions. Chem. Rev. 2011, 111, 6947–6983. DOI: 10.1021/cr200057t.
   PubMed Web of Science ®Google Scholar
• Kobayashi, S.; Ishitani, H. Catalytic Enantioselective Addition to Imines. Chem. Rev. 1999, 99, 1069–1094. DOI: 10.1021/cr980414z.
   PubMed Web of Science ®Google Scholar
• Reddy, S. S.; Reddy, B. R. P.; Reddy, P. V. G. Propylphosphonic Anhydride Catalyzed One-Pot Synthesis of a-Aminonitriles. Chin. Chem. Lett. 2015, 26, 739–743. DOI: 10.1016/j.cclet.2015.03.021.
   Web of Science ®Google Scholar
• Harusawa, S.; Hamada, Y.; Shioiri, T. Diethyl Phosphorocyanidated (DEPC). A Novel Reagent for the Classical Strecker’s a-Aminonitrile Synthesis. Tetrahedron Lett. 1979, 20, 4663–4666. DOI: 10.1016/S0040-4039(01)86677-6.
   Google Scholar
• Nakamura, S.; Sato, N.; Sugimoto, M.; Toru, T. A New Approach to Enantioselective Cyanation of Imines with Et3AlCN. Tetrahedron Asymmetry. 2004, 15, 1513–1516. DOI: 10.1016/j.tetasy.2004.03.040.
   Google Scholar
• Vachal, P.; Jacobsen, E. N. Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction. J. Am. Chem. Soc. 2002, 124, 10012–10014. DOI: 10.1021/ja027246j.
   PubMed Web of Science ®Google Scholar
• Khalaf, E.; Alameri, A. A.; Malviya, J.; Kumar, T. C. A.; Altalbawy, F. M. A.; Alfilh, R. H. C.; Kazemnejadi, M. Synthesis of Highly Porous Mn2O3-Doped Fe3O4 NPs with a Dual Catalytic Function Using Asymmetric Water Soluble Mn-Salen Complex as a Reducing Agent and Template: Catalytic Activity over One-Pot Strecker Synthesis from Alcohols in Recyclable TAIm[CN] Ionic Liquid. Catal. Lett. 2022, 152, 3317–3331. DOI: 10.1007/s10562-022-04210-0.
   Web of Science ®Google Scholar
• Khan, S.; Markad, D.; Mandal, S. K. Two Zn(II)/Cd(II) Coordination Polymers as Recyclable Heterogeneous Catalysts for an Efficient Room-Temperature Synthesis of α-Aminonitriles via the Solvent-Free Strecker Reaction. Inorg. Chem. 2023, 62, 275–284. DOI: 10.1021/acs.inorgchem.2c03369.
   PubMed Web of Science ®Google Scholar
• Das, S.; Kumar, R.; Devadkar, A.; Panda, T. K. Zinc Complexes of β-Ketoiminato Ligands as Efficient Catalysts for the Synthesis of α-Amino Nitriles via Strecker Reaction. Asian J. Org. Chem. 2020, 9, 1217–1224. DOI: 10.1002/ajoc.202000278.
   Web of Science ®Google Scholar
• Reinares-Fisac, D.; Aguirre-Díaz, L. M.; Iglesias, M.; Snejko, N.; Gutiérrez-Puebla, E.; Monge, M. Á.; Gándara, F. A Mesoporous Indium Metal-Organic Framework: Remarkable Advances in Catalytic Activity for Strecker Reaction of Ketones. J. Am. Chem. Soc. 2016, 138, 9089–9092. DOI: 10.1021/jacs.6b05706.
   PubMed Web of Science ®Google Scholar
• Gomez-Oliveira, E. P.; Mendez, N.; Iglesias, M.; Gutierrez-Puebla, E.; Aguirre-Diaz, L. M.; Monge, M. A. Building a Green, Robust, and Efficient Bi-MOF Heterogeneous Catalyst for the Strecker Reaction of Ketones. Inorg. Chem. 2022, 61, 7523–7529. DOI: 10.1021/acs.inorgchem.2c00628.
   PubMed Web of Science ®Google Scholar
• Ramsperger, C. A.; Tufts, N. Q.; Yadav, A. K.; Lessard, J. M.; Stylianou, K. C. Sustainable and Chemoselective Synthesis of α-Aminonitriles Using Lewis and Brønsted Acid-Functionalized Nanoconfined Spaces. ACS Appl. Mater. Interfaces. 2022, 14, 49957–49964. DOI: 10.1021/acsami.2c13945.
   Web of Science ®Google Scholar
• Gupta, V.; Mandal, S. K. Design and Construction of a Chiral Cd(II)-MOF from Achiral Precursors: Synthesis, Crystal Structure and Catalytic Activity toward C-C and C-N Bond Forming Reactions. Inorg. Chem. 2019, 58, 3219–3226. DOI: 10.1021/acs.inorgchem.8b03307.
   PubMed Web of Science ®Google Scholar
• Gupta, V.; Mandal, S. K. A Microporous Metal–Organic Framework Catalyst for Solvent-Free Strecker Reaction and CO2 Fixation at Ambient Conditions. Inorg. Chem. 2020, 59, 4273–4281. DOI: 10.1021/acs.inorgchem.9b03051.
   PubMed Web of Science ®Google Scholar
• Cruz-Acosta, F.; Santos-Exposito, A.; Armas, P.; Garcia-Tellado, F. Lewis Base-Catalyzed Three-Component Strecker Reaction on Water. An Efficient Manifold for the Direct α-Cyanoamination of Ketones and Aldehydes. Chem. Commun. 2009, 45, 6839–6841. DOI: 10.1039/b914151k.
   Web of Science ®Google Scholar
• Sipos, S.; Jablonkai, I. One-Pot Synthesis of α-Aminonitriles from Alkyl and Aryl Cyanides: A Strecker Reaction via Aldimine Alanes. Tetrahedron Lett. 2009, 50, 1844–1846. DOI: 10.1016/j.tetlet.2009.02.004.
   Web of Science ®Google Scholar
• Abell, J. P.; Yamamoto, H. Dual-Activation Asymmetric Strecker Reaction of Aldimines and Ketimines Catalyzed by a Tethered Bis(8-Quinolinolato) Aluminum Complex. J. Am. Chem. Soc. 2009, 131, 15118–15119. DOI: 10.1021/ja907268g.
   PubMed Web of Science ®Google Scholar
• Li, Z.; Ma, Y.; Xu, J.; Shi, J.; Cai, H. One-Pot Three-Component Synthesis of α-Aminonitriles Using Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source. Tetrahedron Lett. 2010, 51, 3922–3926. DOI: 10.1016/j.tetlet.2010.05.088.
   Web of Science ®Google Scholar
• Zhao, Z.; Li, Z. Solvent-Free Chemoselective Cyanation of α,α-Dibromoacetophenones Using Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source. Eur. J. Org. Chem. 2010, 2010, 5460–5463. DOI: 10.1002/ejoc.201000848.
   Web of Science ®Google Scholar
• Li, Z.; Niu, P.; Li, R.; Zhang, Y.; Ma, B.; Yang, J. Cyanoaroylation of Imines Bearing a Thiazole Ring Using Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source. J. Chem. Res. 2012, 36, 709–711. DOI: 10.3184/174751912X13518642070088.
   Web of Science ®Google Scholar
• Li, Z.; Wen, F.; Yang, J. Hydrocyanation of Unsaturated Imines Using Potassium Hexacyanoferrate(II) as a Cyanide Source. Chin. J. Chem. 2014, 32, 1251–1254. DOI: 10.1002/cjoc.201400635.
   Web of Science ®Google Scholar
• Lu, H.; Li, Z. Palladium-Catalyzed One-Pot Four-Component Synthesis of β-Cyano-α,β-Unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source. Adv. Synth. Catal. 2019, 361, 4474–4482. DOI: 10.1002/adsc.201900733.
   Web of Science ®Google Scholar
• Sajadi, S. M.; Maham, M.; Mahmoud, S. A. K4[Fe(CN)6] as Non-Toxic Source of Cyanide for the Cyanation of Aryl Halides Using Pd-Beta Zeolite as a Heterogeneous Catalyst. J. Chem. Res. 2013, 37, 620–622. DOI: 10.3184/174751913X13787959859425.
   Web of Science ®Google Scholar
• Lindstrom, U. M. Stereoselective Organic Reactions in Water. Chem. Rev. 2002, 102, 2751–2772. DOI: 10.1021/cr010122p.
   PubMed Web of Science ®Google Scholar
• Kitanosono, T.; Masuda, K.; Xu, P.; Kobayashi, S. Catalytic Organic Reactions in Water toward Sustainable Society. Chem. Rev. 2018, 118, 679–746. DOI: 10.1021/acs.chemrev.7b00417.
   PubMed Web of Science ®Google Scholar
• Breslow, R. Hydrophobic Effects on Simple Organic Reactions in Water. Acc. Chem. Res. 1991, 24, 159–164. DOI: 10.1021/ar00006a001.
   Web of Science ®Google Scholar
• Han, B.; He, X. H.; Liu, Y. Q.; He, G.; Peng, C.; Li, J. L. Asymmetric Organocatalysis: An Enabling Technology for Medicinal Chemistry. Chem. Soc. Rev. 2021, 50, 1522–1586. DOI: 10.1039/D0CS00196A.
   PubMed Web of Science ®Google Scholar
• Mitra, B.; Ghosh, P. Humic Acid: A Biodegradable Organocatalyst for Solvent-Free Synthesis of Bis(Indolyl)Methanes, Bis(Pyrazolyl)Methanes, Bis-Coumarins and Bis-Lawsones. ChemistrySelect. 2021, 6, 68–81. DOI: 10.1002/slct.202004245.
   Web of Science ®Google Scholar
• Wang, H.; Wang, Y.; Han, Y.; Zhao, W.; Wang, X. Humic Acid as an Efficient and Reusable Catalyst for One Pot Three-Component Green Synthesis of 5-Substituted 2h-Tetrazoles in Water. RSC Adv. 2020, 10, 784–789. DOI: 10.1039/c9ra08523h.
   PubMed Web of Science ®Google Scholar