A New Rapid and Specific Iodination Reagent for Phenolic Compounds
Till Hauenschild, Dariush Hinderberger
Organics · pp. 137–145 · Published 4 Apr 2023
10.3390/org4020011Abstract
A new rapid iodination reagent, N1,N3,N5-tris[(2,4,6-trimethylpyridine)iodo(I)]-2,4,6-triphenyl-s-triazine trihexafluorophosphate, was synthesized in a modification of the established synthesis of 2,4,6-triiodo-3,5-dimethylphenol in the presence of bis(2,4,6-trimethylpyridine)iodo(I) hexafluorophosphate and used for the precise post-modification of mono- and trisubstituted phenyl compounds. We performed triple iodinations with our new phenyl-based compounds as a proof of principle of selected types of phenols, ß-sympatholytic agents and their spin-labeled derivatives, which can be employed in electron paramagnetic resonance (EPR) spectroscopy. The new rapid iodination reagent can be employed with high reactivity and regioselectivity.
References (39)
- 1 Krasnokutskaya, 2007, A New, One-Step, Effective Protocol for the Iodination of Aromatic and Heterocyclic Compounds via Aprotic Diazotization of Amines [DOI]
- 2 Hubbard, 2008, Halo- and Azidodediazoniation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Halides and Trimethylsilyl Azide and Sandmeyer-Type Bromodediazoniation with Cu(I)Br in [BMIM][PF6] Ionic Liquid [DOI]
- 3 Filimonov, 2008, Unusually Stable, Versatile, and Pure Arenediazonium Tosylates: Their Preparation, Structures, and Synthetic Applicability [DOI]
- 4 Filimonov, 2008, Sulfonic Acid Based Cation-Exchange Resin: A Novel Proton Source for One-Pot Diazotization-Iodination of Aromatic Amines in Water [DOI]
- 5 Leas, 2017, One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides [DOI]
- 6 Hauenschild, 2019, A Platform of Phenol-Based Nitroxide Radicals as an “EPR Toolbox” in Supramolecular and Click Chemistry [DOI]
- 7 Thiebes, 1998, Mild Preparation of Haloarenes by Ipso-Substitution of Arylboronic Acids with N-Halosuccinimides [DOI]
- 8 MacNeil, 2001, Selective Ortho and Benzylic Functionalization of Secondary and Tertiary p-Tolylsulfonamides. Ipso-Bromo Desilylation and Suzuki Cross-Coupling Reactions [DOI]
- 9 Klapars, 2002, Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction [DOI]
- 10 Stavber, 2002, Progressive Direct Iodination of Sterically Hindered Alkyl Substituted Benzenes [DOI]
- 11 Castanet, 2002, Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid [DOI]
- 12 Lulinski, 2004, Eco-friendly Oxidative Iodination of Various Arenes with a Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant [1]
- 13 Iskra, 2004, Nonmetal-Catalyzed Iodination of Arenes with Iodide and Hydrogen Peroxide [DOI]
- 14 Prakash, 2004, N-Halosuccinimide/BF3−H2O, Efficient Electrophilic Halogenating Systems for Aromatics [DOI]
- 15 Sedelmeier, 2005, Efficient Copper-Catalyzed N-Arylation of Sulfoximines with Aryl Iodides and Aryl Bromides [DOI]
- 16 Kalyani, 2006, A Simple Catalytic Method for the Regioselective Halogenation of Arenes [DOI]
- 17 Kraszkiewicz, 2006, Oxidative Iodination of Deactivated Arenes in Concentrated Sulfuric Acid with I2/NaIO4 and KI/NaIO4 Iodinating Systems
- 18 Ganguly, 2010, Ecofriendly Iodination of Activated Aromatics and Coumarins Using Potassium Iodide and Ammonium Peroxodisulfate [DOI]
- 19 Qiu, 2010, Gold(III)-Catalyzed Halogenation of Aromatic Boronates with N-Halosuccinimides [DOI]
- 20 Gallo, 2010, Efficient and selective iodination of phenols promoted by iodine and hydrogen peroxide in water [DOI]
- 21 Cobas, 2012, Aryne Insertion into I–I σ-Bonds [DOI]
- 22 Jakab, 2013, Mild and Selective Organocatalytic Iodination of Activated Aromatic Compounds [DOI]
- 23 Du, 2013, Palladium-Catalyzed Highly Selective ortho-Halogenation (I, Br, Cl) of Arylnitriles via sp2 C–H Bond Activation Using Cyano as Directing Group [DOI]
- 24 Partridge, 2013, Sterically Controlled Iodination of Arenes via Iridium-Catalyzed C–H Borylation [DOI]
- 25 Niu, 2014, Metal-Free Iodination of Arylboronic Acids and the Synthesis of Biaryl Derivatives [DOI]
- 26 Leboeuf, 2014, Gold(I)-Catalyzed Iodination of Arenes
- 27 Song, 2015, Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization [DOI]
- 28 Chen, 2015, Imidazolium Salt Catalyzed para-Selective Halogenation of Electron-Rich Arenes [DOI]
- 29 Li, 2015, Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction [DOI]
- 30 Racys, 2015, Highly Regioselective Iodination of Arenes via Iron(III)-Catalyzed Activation of N-Iodosuccinimide [DOI]
- 31 Racys, 2016, Silver(I)-Catalyzed Iodination of Arenes: Tuning the Lewis Acidity of N-Iodosuccinimide Activation [DOI]
- 32 Fu, 2016, Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions [DOI]
- 33 Ajvazi, 2022, Electrophilic Iodination of Organic Compounds Using Elemental Iodine or Iodides: Recent Advances 2008–2021: Part I [DOI]
- 34 Brunei, 1995, Iodination of phenols and anilines with bis(sym-collidine)iodine(I) hexafluorophosphate [DOI]
- 35 Homsi, 2000, Preparation of Bis(2,4,6-Trimethylpyridine)Iodine(I) Hexafluorophosphate and Bis(2,4,6-Trimethylpyridine) Bromine(I) Hexafluorophosphate [DOI]
- 36 Rosenthaler, 1946, Process for preparing and therapeutical applications of the 2,4,6-triiodophenol
- 37 Emmanuvel, 2006, NaIO4/KI/NaCl: A new reagent system for iodination of activated aromatics through in situ generation of iodine monochloride [DOI]
- 38 Hauenschild, 2016, Characterizing Active Pharmaceutical Ingredient Binding to Human Serum Albumin by Spin-Labeling and EPR Spectroscopy [DOI]
- 39 Sultani, 2016, Spin-labelled diketopiperazines and peptide–peptoid chimera by Ugi-multi-component-reactions [DOI]
Cited by 2
Pierre Audebert, Vincent Sol · Progress in heterocyclic chemistry · 2024
Showing 1 of 2 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
Article metrics
Real usage data collected on this platform.
0
Page views
0
PDF downloads
0
Outbound clicks
2
Citations
Views by country
Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".
No views recorded yet.
Traffic sources
Referring site, by host.
No traffic recorded yet.
Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.