Regioselective Transfer Hydrogenative Defluorination of Polyfluoroarenes Catalyzed by Bifunctional Azairidacycle

References (61)

1. 1 Senaweera, 2014, Photocatalytic Hydrodefluorination: Facile Access to Partially, Fluorinated Aromatics [DOI]
2. 2 Weaver, 2014, C−F activation and functionalization of perfluoro- and polyfluoroarenes [DOI]
3. 3 Amii, 2009, C−F Bond Activation in Organic Synthesis [DOI]
4. 4 Liang, 2013, Introduction of Fluorine and Fluorine-Containing Functional Groups [DOI]
5. 5 Campbell, 2015, Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [DOI]
6. 6 Champagne, 2015, Monofluorination of Organic Compounds: 10 Years of Innovation [DOI]
7. 7 Sather, 2016, The Evolution of Pd0/PdII-Catalyzed Aromatic Fluorination [DOI]
8. 8 Szpera, 2019, The Fluorinayion of C–H Bonds: Developments and Perspectives [DOI]
9. 9 See, 2020, Development of SNAr Nucleophilic Fluorination: A Fruitful Academia-Industry Collaboration [DOI]
10. 10 Rozatian, 2021, Reactivities of electrophilic N–F fluorinating reagents [DOI]
11. 11 Kuehnel, 2013, Synthesis of Fluorinated Building Blocks by Transition-Metal-Mediated Hydrodefluorination Reactions [DOI]
12. 12 Whittlesey, 2014, Catalytic Hydrodefluorination with Late Transition Metal Complexes [DOI]
13. 13 Braun, 2015, Hydrodefluorination Reactions Catalyzed by Transition-Metal Complexes
14. 14 Aizenberg, 1994, Catalytic Activation of Carbon-Fluorine Bonds by a Soluble Transition Metal Complex [DOI]
15. 15 Vela, 2005, Synthesis and Reactivity of Low-Coordinate Iron(II) Fluoride Complexes and Their Use in the Catalytic Hydroefluorination of Fluorocarbons [DOI]
16. 16 Reade, 2009, Catalytic Hydrodefluorination of Aromatic Fluorocarbons by Ruthenium N-Heterocyclic Carbene Complexes [DOI]
17. 17 Feliz, 2011, Mechanism of the Catalytic Hydrodefluorination of Pentafluoropyridine by Group Six Triangular Cluster Hydrides Containing Phosphines: A Combined Experimental and Theoretical Study [DOI]
18. 18 Fischer, 2012, Decisive Steps of the Hydrodefluorination of Fluoroaromatics Using [Ni(NHC)2] [DOI]
19. 19 Lv, 2012, π–π Interaction Assisted Hydrodefluorination of Perfluoroarenes by Gold Hydride: A Case of Synergistic Effect on C–F Bond Activation [DOI]
20. 20 Chen, 2013, Palladium-Catalyzed Ortho-Selective C–F Activation of Polyfluoroarenes with Triethylsilane: A Facile Access to Partially Fluorinated Aromatics [DOI]
21. 21 Podolan, 2013, Selective Catalytic Hydrdefluorination as a Key Step for the Synthesis of Hitherto Inaccessible Aminopyridine Derivatives [DOI]
22. 22 2014, On the Catalytic Hydrodefluorination of Fluoroaromatics Using Nickel Complexes: The True Role of the Phosphine [DOI]
23. 23 Hein, 2017, Synthesis and Reactivity of a Low-Coordinate Iron(II) Hydride Complex: Applications in Catalytic Hydrodefluorination [DOI]
24. 24 Yow, 2012, Zirconocene Dichloride Catalyzed Hydrodefluorination of Csp3−F bonds [DOI]
25. 25 Ekkert, 2014, Rhodium Catalyzed, Carbon−Hydrogen Bond Directed Hydrodefluorination of Fluoroarenes [DOI]
26. 26 Aizenberg, 1995, Homogeneous Rhodium Complex-Catalyzed Hydrogenolysis of C–F Bonds [DOI]
27. 27 Edelbach, 1997, Mechanism of Carbon–Fluorine Bond Activation by (C5Me5)Rh(PMe3)H2 [DOI]
28. 28 Young, 1999, Catalytic C–F Bond Activation of Nonactivated Monofluoroarenes [DOI]
29. 29 Braun, 2007, Hydrodefluorination of pentafluoropyridine at rhodium using dihydrogen: Detection of unusual rhodium hydrido complexes [DOI]
30. 30 Konnick, 2013, The Hydroxide-Promoted Catalytic Hydrodefluoriation of Fluorocarbons by Ruthenium in Aqueous Media [DOI]
31. 31 Nakai, 2014, Catalytic C–F Bond Hydrogenolysis of Fluoroaromatics by [(η2-C5Me5)RhI(2,2’-bipyridine)] [DOI]
32. 32 Moore, 2020, Catalytic Hydrogenolysis of Aryl C–F Bonds Using a Bimetallic Rhodium–Indium Complex [DOI]
33. 33 Matsunami, 2016, Hydrodefluorination of Fluoroarenes Using Hydrogen Transfer Catalysts with a Bifunctional Iridium/NH Moiety [DOI]
34. 34 Matsunami, 2018, Hydrogen Evolution from Formic Acid and Hydrodefluorination of Fluoroarenes by Bifunctional Iridium Catalysts—Beyond the Transfer Hydrogenation [DOI]
35. 35 Matsunami, 2018, Nucleophilic Aromatic Substitution in Hydrodefluorination Exemplified by Hydridoiridium(III) Complexes with Fluorinated Phenylsulfonyl-1,2-diphenylethylenediamine Ligands [DOI]
36. 36 Dub, 2013, C−F Bond Breaking through Aromatic Nucleophilic Substitution with a Hydroxo Ligand Mediated via Water Bifunctional Activation [DOI]
37. 37 Dub, 2019, Cleavage of N−H Bond of Ammonia via Metal–Ligand Cooperation Enables Rational Design of a Conceptually New Noyori-Ikariya Catalyst [DOI]
38. 38 McKay, 2015, Mechanistic Study of Ru-NHC-Catalyzed Hydrodefluorination of Fluoropyridines: The Influence of the NHC on the Regioselectivity of C–F Activation and Chemoselectivity of C–F versus C–H Bond Cleavage [DOI]
39. 39 Cybulski, 2017, Room Temperature Regioselective Catalytic Hydrodefluorination of Fluoroarenes with trans-[Ru(NHC)4H2] through a Concerted Nucleophilic Ru–H Attack Pathway [DOI]
40. 40 Paleta, 2010, Regiospecific nucleophilic substitution in 2,3,4,5,6-pentafluorobiphenyl as model compound for supramolecular systems. Theoretical study of transition states and energy profiles, evidence for tetrahedral SN2 mechanism [DOI]
41. 41 Kikushima, K., Koyama, H., Kodama, K., and Dohi, T. (2021). Nucleophilic Aromatic Substitution of Polyfluoroarene to Access Highly Functionalized 10-Phenylphenothiazine Derivatives. Molecules, 26. [DOI]
42. 42 Zimmerman, 1961, Orientation in Metal Ammonia Reduction [DOI]
43. 43 Chambers, 1988, Mechanisms for Reactions of Halogenated Compounds. Part 5. Orientating Effects of Fluorine Substituents on Nucleophilic Substitution in Naphthalene and Other Polycyclic Systems [DOI]
44. 44 Baker, 2010, The Meisenheimer model for predicting the principal site for nucleophilic substitution in aromatic perfluorocarbons—Generalization to include ring-nitrogen atoms and non-fluorine ring substituents [DOI]
45. 45 Liljenberg, 2012, Predicting Regioselectivity in Nucleophilic Aromatic Substitutiton [DOI]
46. 46 Liljenberg, 2013, Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides [DOI]
47. 47 Sadowsky, 2013, Thermochemical Factors Affecting Dehalogenation of Aromatics [DOI]
48. 48 Sadowsky, 2014, Dehalogenation of Aromatics by Nucleophilic Aromatic Substitution [DOI]
49. 49 Crucius, 2012, 1,4,8,11,15,18,22,25-Octafluorophthalocyaninato Zinc (F8PcZn) [DOI]
50. 50 Banks, 1965, Heterocyclic Polyfluoro-Compounds. Part IV. Nucleophilic Substitution in Pentafluoropyridine: The Preparation and Properties of Some 4-Substituted 2,3,5,6-Tetrafluoropyridines [DOI]
51. 51 Schoch, 2021, Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4 [DOI]
52. 52 Beregovaya, 2001, Potential Energy Surface and dissociative cleavage of chlorobenzene radial anion [DOI]
53. 53 Lynch, 2016, A mild hydration of nitriles catalyzed by copper(II) acetate [DOI]
54. 54 Ciganek, 1992, Tertiary Carbinamines by Addition of Organocerium Reagents to Nitriles and Ketimines [DOI]
55. 55 Arita, 2008, Synthesis and Reactivities of Cp*Ir Amide and Hydride Complexes Bearing C−N Chelate Ligands [DOI]
56. 56 Sato, Y., Kawata, Y., Yasui, S., Kayaki, Y., and Ikariya, T. (2021). New Bifunctional Bis(azairidacycle) with Axial Chirality via Double Cyclometalation of 2,2’-Bis(aminomethyl)-1,1’-binaphthyl. Molecules, 26. [DOI]
57. 57 Kumar, 2019, Optimization of N-benzyl-5-nitrofuran-2-carboxamide as an antitubercular agent [DOI]
58. 58 Jaudzems, 2014, Plasmepsin Inhibitory Activity and Structure-Guided Optimization of a Potent Hydroxyethylamine-Based Antimalarial Hit [DOI]
59. 59 Rigaku Coorporation (2015). CrystalStructure 4.1: Crystal Structure Analysis Package, Rigaku Coorporation.
60. 60 Altomare, 1994, SIR92—A program for automatic solution of crystal structures by direct methods
61. 61 Sheldrick, 2015, Crystal structure refinement with SHELXL [DOI]

Cited by 4

Showing 2 of 4 known citations — external sources report more than can currently be individually listed.

Related research

• A Novel Catalytic Synthesis of Flavones under Autoclave Conditions and Comparative Study of Anti-cancer Activity — shares topic coverage
• Thermostability and in-vitro Antibacterial Activity of Aqueous Extracts of Tetrapleura tetraptera Pods on Multidrug Resistant Clinical Isolates — shares topic coverage
• Acute Toxicity, Phytochemistry and Anti-diarrheal Effects of Celtis integrifolia Lam. Aqueous Leaf Extract in Wistar Albino Rats — shares topic coverage
• Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective — shares topic coverage
• Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory — shares topic coverage