Palladium-catalyzed hydrogenations in dichloromethane

References

• Rylander, P. N. In Catalysis in Organic Synthesis; Jones, W. H., Ed.; Academic Press, Inc.: New York, 1980, pp 155–171.
   Google Scholar
• Rajadhyaksha, R. A.; Karwa, S. L. Solvent Effects in Catalytic Hydrogenation. Chem. Eng. Sci. 1986, 41, 1765–1770. DOI: 10.1016/0009-2509(86)87055-5.
   Web of Science ®Google Scholar
• Fannes, C.; Verbruggen, S.; Janssen, B.; Egle, B. Influence of Solvents and Additives on the Pyrophoricity of Palladium on Carbon Catalyst after Hydrogenation. Org. Process Res. Dev. 2021, 25, 2438–2441. DOI: 10.1021/acs.oprd.1c00190.
   Web of Science ®Google Scholar
• Hegedűs, L.; Máthé, T.; Tungler, A. Hydrogenation of Pyrrole Derivatives. Part IV. Hydrogenation of 1-Methylpyrrole. Appl. Catal. A Gen. 1997, 152, 143–151. DOI: 10.1016/S0926-860X(96)00359-6.
   Web of Science ®Google Scholar
• Hegedűs, L.; Máthé, T. Selective Heterogeneous Catalytic Hydrogenation of Nitriles to Primary Amines in Liquid Phase. Part I. Hydrogenation of Benzonitrile over Palladium. Appl. Catal. A Gen. 2005, 296, 209–215. DOI: 10.1016/j.apcata.2005.08.024.
   Web of Science ®Google Scholar
• Hegedűs, L.; Máthé, T.; Kárpáti, T. Selective Heterogeneous Catalytic Hydrogenation of Nitriles to Primary Amines in Liquid Phase. Part II. Hydrogenation of Benzyl Cyanide over Palladium. Appl. Catal. A Gen. 2008, 349, 40–45. DOI: 10.1016/j.apcata.2008.07.012.
   Web of Science ®Google Scholar
• Farkas, F.; Thurner, A.; Kovács, E.; Faigl, F.; Hegedűs, L. Hydrogenolysis of O-Protected Hydroxyoxetanes over Palladium: An Efficient Method for a One-Step Ring Opening and Detritylation Reaction. Catal. Commun. 2009, 10, 635–639. DOI: 10.1016/j.catcom.2008.11.007.
   Web of Science ®Google Scholar
• Kovács, E.; Thurner, A.; Farkas, F.; Faigl, F.; Hegedűs, L. Hydrogenolysis of N-Protected Aminooxetanes over Palladium: An Efficient Method for a One-Step Ring Opening and Debenzylation Reaction. J. Mol. Catal. A Chem. 2011, 339, 32–36. DOI: 10.1016/j.molcata.2011.02.008.
   Google Scholar
• Kovács, E.; Faigl, F.; Mucsi, Z.; Nyerges, M.; Hegedűs, L. Hydrogenolysis of N- and O-Protected Hydroxyazetidines over Palladium: Efficient and Selective Methods for Ring Opening and Deprotecting Reactions. J. Mol. Catal. A Chem. 2014, 395, 217–224. DOI: 10.1016/j.molcata.2014.08.027.
   Google Scholar
• Tungler, A.; Szabados, E. Overcoming Problems at Elaboration and Scale-up of Liquid-Phase Pd/C Mediated Catalytic Hydrogenations in Pharmaceutical Production. Org. Process Res. Dev. 2016, 20, 1246–1251. DOI: 10.1021/acs.oprd.6b00073.
   Web of Science ®Google Scholar
• Lévay, K.; Tóth, K. D.; Kárpáti, T.; Hegedűs, L. Heterogeneous Catalytic Hydrogenation of 3-Phenylpropionitrile over Palladium on Carbon. ACS Omega 2020, 5, 5487–5497. DOI: 10.1021/acsomega.0c00125.
   PubMed Web of Science ®Google Scholar
• Lévay, K.; Kárpáti, T.; Hegedűs, L. Selective Hydrogenation of Benzonitrile and Its Homologues to Primary Amines over Platinum. J. Ind. Eng. Chem. 2021, 101, 279–292. DOI: 10.1016/j.jiec.2021.06.002.
   Web of Science ®Google Scholar
• Lévay, K.; Madarász, J.; Hegedűs, L. Tuning the Chemoselectivity of the Pd-Catalyzed Hydrogenation of Pyridinecarbonitriles: An Efficient and Simple Method for Preparing Pyridyl- or Piperidylmethylamines. Catal. Sci. Technol. 2022, 12, 2634–2648. DOI: 10.1039/D1CY02295D.
   Web of Science ®Google Scholar
• Hegedűs, L.; Máthé, T.; Tungler, A. Hydrogenation of Pyrrole Derivatives. Part III. Hydrogenation of Methyl 1-Methyl-2-Pyrroleacetate. Appl. Catal. A Gen. 1997, 153, 133–139. DOI: 10.1016/S0926-860X(96)00332-8.
   Web of Science ®Google Scholar
• Villemin, D.; Letulle, M. Hydrogenation Catalysed by Palladium or Rhodium Chlorides in the Presence of TDA-1. Synth. Commun. 1989, 19, 2833–2839. DOI: 10.1080/00397918908052671.
   Web of Science ®Google Scholar
• Vanier, G. S. Simple and Efficient Microwave-Assisted Hydrogenation Reactions at Moderate Temperature and Pressure. Synlett 2007, 131–135. DOI: 10.1055/s-2006-958428.
   Web of Science ®Google Scholar
• Hegedűs, L.; Miskolczi, S.; Bánsághi, G.; Székely, E.; Faigl, F. Synthesis of (S)-(+)-2-(N-Benzylamino)Butan-1-ol from Its Schiff Base by Catalytic Hydrogenation over Palladium. Curr. Green Chem. 2015, 2, 312–318. DOI: 10.2174/2213346102666150211001310.
   Google Scholar
• Wei, Z.; Pan, R.; Hou, Y.; Yang, Y.; Liu, Y. Graphene-Supported Pd Catalyst for Highly Selective Hydrogenation of Resorcinol to 1,3-Cyclohexanedione through Giant p-Conjugate Interactions. Sci. Rep. 2015, 5, 15664. DOI: 10.1038/srep15664.
   PubMed Web of Science ®Google Scholar
• Hugelshofer, C. L.; Palani, V.; Sarpong, R. Calyciphylline B-Type Alkaloids: Total Syntheses of (-)-Daphlongamine H and (-)-Isodaphlongamine H. J. Am. Chem. Soc. 2019, 141, 8431–8435. DOI: 10.1021/jacs.9b03576.
   PubMed Web of Science ®Google Scholar
• Gordon, A. J.; Ford, R. A. The Chemist’s Companion; J. Wiley & Sons: New York, 1972, pp 442–443.
   Google Scholar
• Felpin, F.-X.; Coste, J.; Zakri, C.; Fouquet, E. Preparation of 2-Quinolones by Sequential Heck Reduction-Cyclization (HRC) Reactions by Using a Multitask Palladium Catalyst. Chem-Eur. J. 2009, 15, 7238–7245. DOI: 10.1002/chem.200900583.
   PubMed Web of Science ®Google Scholar
• Pandarus, V.; Gingras, G.; Béland, F.; Ciriminna, R.; Pagliaro, M. Selective Hydrogenation of Alkenes under Ultramild Conditions. Org. Process Res. Dev. 2012, 16, 1230–1234. DOI: 10.1021/op300079z.
   Web of Science ®Google Scholar
• Lash, T. D.; Marron, T. G.; Bastian, J. A. Porphyrins with Exocyclic Rings. Part 23: Synthesis of Porphyrins with Large Exocyclic Rings—Cyclohexadeca[b]Pyrroles and Porphyrins Therefrom. Tetrahedron 2007, 63, 12343–12351. DOI: 10.1016/j.tet.2007.09.060.
   Web of Science ®Google Scholar
• Taher, E. S.; Guest, P.; Benton, A.; Ma, X.; Banwell, M. G.; Willis, A. C.; Seiser, T.; Newton, T. W.; Hutzler, J. The Synthesis of Certain Phomentrioloxin a Analogues and Their Evaluation as Herbicidal Agents. J. Org. Chem. 2017, 82, 211–233. DOI: 10.1021/acs.joc.6b02372.
   PubMed Web of Science ®Google Scholar
• Mori, A.; Mizusaki, T.; Miyakawa, Y.; Ohashi, E.; Haga, T.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Chemoselective Hydrogenation Method Catalyzed by Pd/C Using Diphenylsulfide as a Reasonable Catalyst Poison. Tetrahedron 2006, 62, 11925–11932. DOI: 10.1016/j.tet.2006.09.094.
   Web of Science ®Google Scholar
• Jones, R. V.; Godorhazy, L.; Varga, N.; Szalay, D.; Urge, L.; Darvas, F. Continuous-Flow High Pressure Hydrogenation Reactor for Optimization and High-Throughput Synthesis. J. Comb. Chem. 2006, 8, 110–116. DOI: 10.1021/cc050107o.
   PubMedGoogle Scholar
• Xu, L.; Sun, S.; Zhang, X.; Gao, H.; Wang, W. Study on the Selective Hydrogenation of Isophorone. RSC Adv. 2021, 11, 4465–4471. DOI: 10.1039/D0RA08107H.
   PubMed Web of Science ®Google Scholar
• Lakshmi Kantam, M.; Parsharamulu, T.; Manorama, S. V. Layered Double Hydroxides Supported Nano Palladium: An Efficient Catalyst for the Chemoselective Hydrogenation of Olefinic Bonds. J. Mol. Catal. A Chem. 2012, 365, 115–119.
   Google Scholar
• Su, X.; Sun, Y.; Yao, J.; Chen, H.; Chen, C. Acid-Promoted Bicyclization of Arylacetylenes to Benzobicyclo[3.2.1]Octanes through Cationic Rearrangements. Chem. Commun. 2016, 52, 4537–4540. DOI: 10.1039/C6CC00452K.
   PubMed Web of Science ®Google Scholar
• Giancotti, G.; Cancellieri, M.; Balboni, A.; Giustiniano, M.; Novellino, E.; Delang, L.; Neyts, J.; Leyssen, P.; Brancale, A.; Bassetto, M. Rational Modifications on a Benzylidene-Acrylohydrazide Antiviral Scaffold, Synthesis and Evaluation of Bioactivity against Chikungunya Virus. Eur. J. Med. Chem. 2018, 149, 56–68. DOI: 10.1016/j.ejmech.2018.02.054.
   PubMed Web of Science ®Google Scholar
• Toneto Novaes, L. F.; Martins Avila, C.; Pelizzaro-Rocha, K. J.; Vendramini-Costa, D. B.; Pereira Dias, M.; Barbosa Trivella, D. B.; Ernesto de Carvalho, J.; Ferreira-Halder, C. V.; Pilli, R. A. (-)-Tarchonanthuslactone: Design of New Analogues, Evaluation of Their Antiproliferative Activity on Cancer Cell Lines, and Preliminary Mechanistic Studies. ChemMedChem 2015, 10, 1687–1699. DOI: 10.1002/cmdc.201500246.
   PubMed Web of Science ®Google Scholar
• Giblin, G. Pyrrole Compounds for the Treatment of Prostaglandin Mediated Diseases. PCT Int. Appl. 2003, 2003101959.
   Google Scholar
• Klövekorn, P.; Pfaffenrot, B.; Juchum, M.; Selig, R.; Albrecht, W.; Zender, L.; Laufer, S. A. From off-to on-Target: New BRAF-Inhibitor-Template-Derived Compounds Selectively Targeting Mitogen Activated Protein Kinase 4 (MKK4). Eur. J. Med. Chem. 2021, 210, 112963. DOI: 10.1016/j.ejmech.2020.112963.
   PubMed Web of Science ®Google Scholar
• Navath, S.; Rao, V.; Woodford, R. T.; Midura-Kiela, M. T.; Ahad, A. M.; Alleti, R.; Kiela, P. R.; Mash, E. A. Design, Synthesis, and Testing of a Molecular Truck for Colonic Delivery of 5-Aminosalicylic Acid. ACS Med. Chem. Lett. 2012, 3, 710–714. DOI: 10.1021/ml300086c.
   PubMed Web of Science ®Google Scholar
• Kollár, L.; Tőrös, S.; Heil, B.; Tuba, Z. Stereoselective Reduction of Steroids with in Situ Prepared Phosphine Rhodium Catalysts. J. Mol. Catal. 1988, 47, 33–39. DOI: 10.1016/0304-5102(88)85070-3.
   Google Scholar
• Kutney, J. P.; Piotrowska, K.; Somerville, J.; Huang, S.-P.; Rettig, S. J. The Chemistry of Thujone. XIII. Synthetic Studies in the Digitoxigenin Series. Can. J. Chem. 1989, 67, 580–589. DOI: 10.1139/v89-088.
   Web of Science ®Google Scholar
• Beck, W.; Kaye, I. A.; Kogon, I. C.; Klein, H. C.; Burlant, W. J. 1-Phenyl-2-(N-methyl-N-Benzylamino)Ethanol and Related Compounds. J. Org. Chem. 1951, 16, 1434–1441. DOI: 10.1021/jo50003a015.
   Web of Science ®Google Scholar
• The use of water as a single solvent in catalytic hydrogenations has been reported; see Takale, B. S.; Thakore, R. R.; Gao, E. S.; Gallou, F.; Lipshutz, B. H. Environmentally Responsible, Safe, and Chemoselective Catalytic Hydrogenation of Olefins: ppm Level Pd Catalysis in Recyclable Water at Room Temperature. Green Chem. 2020, 22, 6055–6061. DOI: 10.1039/D0GC02087G.
   Web of Science ®Google Scholar
• Bruhn, J.; Heimgartner, H.; Schmid, H. The Cope Rearrangement, A Reaction for Repeatable Ring Expansions. Helv. Chim. Acta 1979, 62, 2630–2654. DOI: 10.1002/hlca.19790620814.
   Web of Science ®Google Scholar
• Schmidt, B.; Hölter, F.; Berger, R.; Jessel, S. Mizoroki-Heck Reactions with 4-Phenoldiazonium Salts. Adv. Synth. Catal. 2010, 352, 2463–2473. DOI: 10.1002/adsc.201000493.
   Web of Science ®Google Scholar