AI Article Synopsis
- Hypervalent iodine compounds are eco-friendly and cost-effective alternatives to transition metal catalysts in organic synthesis, offering mild and nontoxic catalytic properties.
- These iodine compounds can facilitate the formation of various chemical bonds (C-N, C-O, C-S, C-F, C-C) through oxidative functionalizations.
- The review discusses recent advancements in using iodine(III) and iodine(V) catalysts, including their application in chiral synthesis and support on different materials like polymers and magnetic nanoparticles.
Article Abstract
Hypervalent iodine compounds as environmentally friendly and relatively inexpensive reagents have properties similar to transition metals. They are employed as alternatives to transition metal catalysts in organic synthesis as mild, nontoxic, selective and recyclable catalytic reagents. Formation of C-N, C-O, C-S, C-F and C-C bonds can be seamlessly accomplished by hypervalent iodine catalysed oxidative functionalisations. The aim of this review is to highlight recent developments in the utilisation of iodine(III) and iodine(V) catalysts in the synthesis of a wide range of organic compounds including chiral catalysts for stereoselective synthesis. Polymer-, magnetic nanoparticle- and metal organic framework-supported hypervalent iodine catalysts are also described.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d2cs00206j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis and Resolution of 4'-Substituted Nucleosides with Potential Antiviral and Antisense Strategies.
J Org Chem
January 2025
Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Komatsushima 4-4-1, Aoba-ku, Sendai 981-8558, Japan.
Nucleoside derivatives having a 4-substituent show promise as potential antiviral agents as well as nucleoside units for constructing nucleic acid medicines. To develop new nucleosides, it is crucial to achieve feasible access to the intended derivatives, encompassing both enantiomers. Toward this end, we started synthesizing an achiral 4-hydroxymethyldihydrofuran as a sugar precursor, which we subjected to the oxidative glycosylation reaction using hypervalent iodine.
View Article and Find Full Text PDFSynthesis and Reactivity of Six-Membered Cyclic Diaryl λ3-Bromanes and λ3-Chloranes.
Angew Chem Int Ed Engl
January 2025
Cardiff University, School of Chemistry, Park Place, Main Building, CF10 3AT, Cardiff, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
Despite the remarkable advancements in hypervalent iodine chemistry, exploration of bromine and chlorine analogues remains in its infancy due to their difficult synthesis. Herein, we introduce six-membered cyclic λ3-bromanes and λ3-chloranes. Through single-crystal X-ray structural analyses and conformational studies, we delineate the crucial bonding patterns pivotal for the thermodynamic stability of these compounds.
View Article and Find Full Text PDFTransition-metal-free dibenzoxazepinone synthesis by hypervalent iodine-mediated chemoselective arylocyclizations of -functionalized salicylamides.
Chem Commun (Camb)
January 2025
College of Pharmaceutical Sciences, Ritsumeikan University, Kusatsu 525-8577, Shiga, Japan.
We have developed transition-metal-free synthetic methodologies for dibenzoxazepinones utilizing salicylamides as starting materials and employing two distinct types of successive hypervalent iodine-mediated arylocyclizations. This synthetic protocol encompasses selective phenol -arylation of salicylamides with diaryliodonium salts, followed by electrophilic aromatic amination utilizing chemically or electronically generated hypervalent iodine reagents in the second stage of the process.
View Article and Find Full Text PDFDirect Synthesis of 2-(4-Hydroxyphenoxy)benzamide Derivatives from 2-Aryloxybenzamide via PhIO-Mediated Oxidation Reaction.
Molecules
December 2024
School of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, China.
The 2-(4-hydroxyphenoxy)benzamide scaffold is frequently found in a variety of bioactive compounds, displaying a broad spectrum of properties, such as antibacterial and antitumor effects. In this study, we developed a new method for synthesizing 2-(4-hydroxyphenoxy)benzamide derivatives from 2-aryloxybenzamide via a PhIO-mediated oxidation reaction. The optimal reaction conditions were established as follows: TFA was used as the solvent, PhIO served as the oxidant with a substrate-to-oxidant ratio of 1:2, and the reaction was conducted at room temperature.
View Article and Find Full Text PDFReactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts.
Beilstein J Org Chem
December 2024
LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA FCT , 2829-516 Caparica, Portugal.
The reactivity of our recently disclosed hypervalent iodine reagents (HIRs) bearing a benzylamine with in situ-generated sulfenate salts was investigated. Under the studied conditions sulfonamides have been obtained in up to 52% yield. This reaction has been extended to a variety of HIRs and sulfenate salts to explore the different reactivity of these new reagents.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!