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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 4
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Articles

Development of [3]ferrocenophane-derived N/B frustrated Lewis pairs for the metal-free catalytic hydrogenation of imines

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Pages 522-528 | Received 10 Sep 2018, Published online: 23 Jan 2019

References

  • (a) Blaser, H. U. ; Burkhardt, S. ; Kirner, H. J. ; Mössner, T. ; Studer, M. ; Ethyl 2,4-Dioxo-4-phenylbutyrate: A Versatile Intermediate for the Large-Scale Preparation of EnantiomericallyPure α-Hydroxy and α-Amino Acid Esters. Synthesis. 2003, 2003, 1679-1682.; (b) Blaser, H. U. ; Schmidt, E. ; Wiley, V. C. H . Weinheim. 2004, 91-103.; (c) Nugent, T. C. ; Ghosh, A. K. ; Wakchaure, V. N. ; Mohanty, R. R . Asymmetric Reductive Amination: Convenient Access to Enantioenriched Alkyl-Alkyl or Aryl-Alkyl Substituted α-Chiral Primary Amines. Adv. Synth. Catal. 2006, 348, 1289-1299.
  • Szeto, K. C. ; Sahyoun, W. ; Merle, N. ; Castelbou, J. L. ; Popoff, N. ; Lefebvre, F. ; Raynaud, J. ; Godard, C. ; Claver, C. ; Delevoye, L. ; et al. Development of Silica-supported Frustrated Lewis Pairs: Highly Active Transition Metal-free Catalysts for the Z-selective Reduction of Alkynes. Catal. Sci. Technol. 2016, 6, 882-889.
  • (a) Welch, G. C. ; Juan, R. R. S. ; Masuda, J. D. ; Stephan, D. W. ; Reversible, Metal-Free Hydrogen Activation. Science. 2006, 314, 1124-1126.; (b) Stephan, D. W. ; Science. 2016, 3. 1248-1256.; (c) Yin, Q. ; Klare, H. F. T. ; Oestreich, M. ; Catalytic Friedel-Crafts C-H Borylation of Electron-Rich Arenes: Dramatic Rate Acceleration by Added Alkenes. Angew. Chem., Int. Ed. 2017, 56, 3712-3717.; (d) Willms, A. ; Schumacher, H. ; Tabassum, H. ; Qi, L. ; Scott, S. L. ; Hausoul, P. J. C. ; Rose, M . Solid Molecular Frustrated Lewis Pairs in a Polyamine Organic Framework for the Catalytic Metal-free Hydrogenation of Alkenes. ChemCatChem. 2018, 10, 1835-1843.; (e) Meng, W. ; Feng, X. ; Du, H . Frustrated Lewis Pairs Catalyzed Asymmetric Metal-Free Hydrogenations and Hydrosilylations. Acc. Chem. Res. 2018, 51, 191-201.
  • (a) Stephan, D. W. ; Greenberg, S. ; Graham, T. W. ; Chase, P. ; Hastie, J. J. ; Geier, S. J. ; Farrell, J. M. ; Brown, C. C. ; Heiden, Z. M. ; Welch, G. C. ; et al. Metal-Free Catalytic Hydrogenation of Polar Substrates by Frustrated Lewis Pairs. Inorg. Chem. 2011, 50, 12338-12348.; (b) Stephan, D. W. Frustrated Lewis Pair” Hydrogenations. Org. Biomol. Chem. 2012, 10, 5740-5746.; (c) Soós, T . Design of Frustrated Lewis Pair Catalysts for Metal-free and Selective Hydrogenation. Pure Appl. Chem. 2011, 83, 667-675.; (d) Paradies, J . Frustrated Lewis Pair Catalyzed Hydrogenations. Synlett. 2013, 24, 777-780.; (e) Hounjet, L. J. ; Stephan, D. W . Hydrogenation by Frustrated Lewis Pairs: Main Group Alternatives to Transition Metal Catalysts? Org. Process Res. Dev 2014, 18, 385-391.; (f) Shi, L. ; Zhou, Y.-G . Enantioselective Metal-Free Hydrogenation Catalyzed by Chiral Frustrated Lewis Pairs. ChemCatChem. 2015, 7, 54-56.
  • (a) Welch, G. C. ; Stephan, D. W . Facile Heterolytic Cleavage of Dihydrogen by Phosphines and Boranes. J. Am. Chem. Soc. 2007, 129, 1880-1881.; (b) Wang, H. ; Fröhlich, R. ; Kehr, G. ; Erker, G . Chem. Commun. 2008, 45, 5966-5968.; (c) Wang, G. ; Chen, C. ; Du, T. ; Zhong, W . Metal-Free Catalytic Hydrogenation of Imines with Recyclable [2.2]Paracyclophane-Derived Frustrated Lewis Pairs Catalysts. Adv. Synth. Catal. 2014, 356, 1747-1752.; (d) Jian, Z. ; Krupski, S. ; Škoch, K. ; Kehr, G. ; Daniliuc, C. G. ; Císařová, I. ; Štěpnička, P. ; Erker, G . Phosphine-Borane Frustrated Lewis Pairs Derived from a 1,1′-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis. Organometallics 2017, 36, 2940-2946.
  • Sumerin, V. ; Schulz, F. ; Nieger, M. ; Leskelä, M. ; Repo, T. ; Rieger, B . Facile Heterolytic H2 Activation by Amines and B(C6F5)3. Angew. Chem. Int. Ed. Engl. 2008, 47, 6001-6003.
  • Geier, S. J. ; Stephan, D. W . Lutidine/B(C6F5)3: At the Boundary of Classical and Frustrated Lewis Pair Reactivity. J. Am. Chem. Soc. 2009, 131, 3476-3477.
  • Inés, B. ; Palomas, D. ; Holle, S. ; Steinberg, S. ; Nicasio, J. A. ; Alcarazo, M . Metal-free Hydrogenation of Electron-poor Allenes and Alkenes. Angew. Chem. Int. Ed. Engl. 2012, 51, 12367-12369.
  • Rajappa, M. ; Shashikala, K. N. ; Achanath, R. ; Chheda, A . Process for the preparation of sertraline hydrochloride form ii. WO Patent 2006027658, 2006.
  • Chen, C. ; Fröhlich, R. ; Kehr, G. ; Erker, G . Structural Features of Lithio[3]ferrocenophane Systems Bearing Stabilizing Dimethylamino Substituents. Organometallics 2008, 27, 3248-3253.

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