Various α-Oxygen Functionalizations of β-Dicarbonyl Compounds Mediated by the Hypervalent Iodine(III) Reagentp-Iodotoluene Difluoride with Different Oxygen-Containing Nucleophiles

2010 ◽  
Vol 352 (2-3) ◽  
pp. 531-546 ◽  
Author(s):  
Jun Yu ◽  
Jun Tian ◽  
Chi Zhang
Keyword(s):  
Hypervalent Iodine ◽  
Dicarbonyl Compounds

scholarly journals Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes

2017 ◽  
Vol 70 (4) ◽  
pp. 430 ◽  
Author(s):  
Ciputra Tejo ◽  
Davin Tirtorahardjo ◽  
David Philip Day ◽  
Dik-Lung Ma ◽  
Chung-Hang Leung ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Hypervalent Iodine ◽  
Atmospheric Conditions ◽  
Dicarbonyl Compounds ◽  
Brønsted Base

The synthesis of α,α-diacylaziridines and α,α,β-triacylaziridines from reaction of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds with arylsulfonyliminoiodinanes (ArSO2N=IPh) under Brønsted base-mediated atmospheric conditions is described. The reaction mechanism is thought to involve the formal oxidation of the substrate followed by aziridination of the ensuing α,β-unsaturated intermediate by the hypervalent iodine(iii) reagent.

scholarly journals Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2116 ◽  
Author(s):  
Jianlin Han ◽  
Greg Butler ◽  
Hiroki Moriwaki ◽  
Hiroyuki Konno ◽  
Vadim A. Soloshonok ◽  
...  
Keyword(s):  
Review Article ◽  
Hypervalent Iodine ◽  
Dicarbonyl Compounds ◽  
Unsaturated Ketones ◽  
Electrophilic Fluorination ◽  
Iodine Compounds ◽  
Styrene Derivatives ◽  
In Situ Generation ◽  
Synthetic Application

This review article focused on the innovative procedure for electrophilic fluorination using HF and in situ generation of the required electrophilic species derived from hypervalent iodine compounds. The areas of synthetic application of this approach include fluorination of 1,3-dicarbonyl compounds, aryl-alkyl ketones, styrene derivatives, α,β-unsaturated ketones and alcohols, homoallyl amine and homoallyl alcohol derivatives, 3-butenoic acids and alkynes.

α-Sulfonyloxylation of 1,3-dicarbonyl compounds utilizing hypervalent iodine(iii) reagent: Construction of quaternary carbon center

2018 ◽  
Vol 48 (15) ◽  
pp. 1957-1965 ◽  
Author(s):  
Ruojuan Liu ◽  
Junzheng Wang ◽  
Wen Hu ◽  
Xiaohui Zhang ◽  
Yan Xiong
Keyword(s):  
Hypervalent Iodine ◽  
Quaternary Carbon ◽  
Dicarbonyl Compounds

ChemInform Abstract: Hypervalent Iodine Oxidation: α-Functionalization of β-Dicarbonyl Compounds Using Iodosobenzene.

ChemInform ◽  
1988 ◽  
Vol 19 (30) ◽  
Author(s):  
R. M. MORIARTY ◽  
R. K. VAID ◽  
V. T. RAVIKUMAR ◽  
B. K. VAID ◽  
T. E. HOPKINS
Keyword(s):  
Hypervalent Iodine ◽  
Dicarbonyl Compounds

Hypervalent iodine oxidation: α-Functionalization of β-dicarbonyl compounds using iodosobenzene

Tetrahedron ◽  
1988 ◽  
Vol 44 (6) ◽  
pp. 1603-1607 ◽  
Author(s):  
Robert M. Moriarty ◽  
Radhe K. Vaid ◽  
Vasulinga T. Ravikumar ◽  
Beena K. Vaid ◽  
Thomas E. Hopkins
Keyword(s):  
Hypervalent Iodine ◽  
Dicarbonyl Compounds

Dicarbonyl derived post-translational modifications: chemistry bridging biology and aging-related disease

2020 ◽  
Vol 64 (1) ◽  
pp. 97-110
Author(s):  
Christian Sibbersen ◽  
Mogens Johannsen
Keyword(s):  
Mass Spectrometry ◽  
Future Research ◽  
Amino Acid Residues ◽  
Post Translational Modification ◽  
Dicarbonyl Compounds ◽  
Protein Targets ◽  
Post Translational Modifications ◽  
Reactive Protein ◽  
Glycation End Products ◽  
Direct Mass Spectrometry

Abstract In living systems, nucleophilic amino acid residues are prone to non-enzymatic post-translational modification by electrophiles. α-Dicarbonyl compounds are a special type of electrophiles that can react irreversibly with lysine, arginine, and cysteine residues via complex mechanisms to form post-translational modifications known as advanced glycation end-products (AGEs). Glyoxal, methylglyoxal, and 3-deoxyglucosone are the major endogenous dicarbonyls, with methylglyoxal being the most well-studied. There are several routes that lead to the formation of dicarbonyl compounds, most originating from glucose and glucose metabolism, such as the non-enzymatic decomposition of glycolytic intermediates and fructosyl amines. Although dicarbonyls are removed continuously mainly via the glyoxalase system, several conditions lead to an increase in dicarbonyl concentration and thereby AGE formation. AGEs have been implicated in diabetes and aging-related diseases, and for this reason the elucidation of their structure as well as protein targets is of great interest. Though the dicarbonyls and reactive protein side chains are of relatively simple nature, the structures of the adducts as well as their mechanism of formation are not that trivial. Furthermore, detection of sites of modification can be demanding and current best practices rely on either direct mass spectrometry or various methods of enrichment based on antibodies or click chemistry followed by mass spectrometry. Future research into the structure of these adducts and protein targets of dicarbonyl compounds may improve the understanding of how the mechanisms of diabetes and aging-related physiological damage occur.

Oxidase Catalysis via an Aerobically Generated Dess-Martin Periodinane Analogue

2018 ◽  
Author(s):  
Asim Maity ◽  
Sung-Min Hyun ◽  
Alan Wortman ◽  
David Powers
Keyword(s):  
Chemical Synthesis ◽  
Aerobic Oxidation ◽  
Substrate Oxidation ◽  
Oxidation Catalysis ◽  
Hypervalent Iodine ◽  
Oxidation Reactions ◽  
Broad Array ◽  
Oxidation Chemistry ◽  
Reactive Oxidants

<p>Hypervalent iodine(V) reagents, such as Dess-Martin periodinane (DMP) and 2-iodoxybenzoic acid (IBX), are broadly useful oxidants in chemical synthesis. Development of strategies to access these reagents from O2 would immediately enable use of O2 as a terminal oxidant in a broad array of substrate oxidation reactions. Recently we disclosed the aerobic synthesis of I(III) reagents by intercepting reactive oxidants generated during aldehyde autoxidation. Here, we couple aerobic oxidation of iodobenzenes with disproportionation of the initially generated I(III) compounds to generate I(V) reagents. The aerobically generated I(V) reagents exhibit substrate oxidation chemistry analogous to that of DMP. Further, the developed aerobic generation of I(V) has enabled the first application of I(V) intermediates in aerobic oxidation catalysis.</p>

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