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 Iminoiodane- and Brønsted Base-Mediated Cross Dehydrogenative Coupling of Cyclic Ethers with 1,3-Dicarbonyl Compounds

Molecules ◽  
2015 ◽  
Vol 20 (7) ◽  
pp. 13336-13353 ◽  
Author(s):  
Ciputra Tejo ◽  
Xiao Sim ◽  
Bo Lee ◽  
Benjamin Ayers ◽  
Chung-Hang Leung ◽  
...  
Keyword(s):  
Cyclic Ethers ◽  
Dicarbonyl Compounds ◽  
Dehydrogenative Coupling ◽  
Brønsted Base

Iodosobenzene-Mediated α-Acyloxylation of 1,3-Dicarbonyl Compounds with Carboxylic Acids and Insight into the Reaction Mechanism

2018 ◽  
Vol 83 (5) ◽  
pp. 2904-2911 ◽  
Author(s):  
Chitturi Bhujanga Rao ◽  
Jingwen Yuan ◽  
Qian Zhang ◽  
Rui Zhang ◽  
Ning Zhang ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Dicarbonyl Compounds ◽  
Insight Into

scholarly journals Revisiting the effect of f ‐functions in predicting the right reaction mechanism for hypervalent iodine reagents

2020 ◽  
Author(s):  
Tian‐Yu Sun ◽  
Kai Chen ◽  
Huakang Zhou ◽  
Tingting You ◽  
Penggang Yin ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Hypervalent Iodine ◽  
The Right

A novel type rearrangement in cyclic β-dicarbonyl compounds in strong acid media

1981 ◽  
Vol 59 (12) ◽  
pp. 1717-1721 ◽  
Author(s):  
Kimitoshi Saito ◽  
Hidetaka Yuki ◽  
Toshiyuki Ohyama ◽  
Ryohei Nakane ◽  
Katsuyuki Nagumo ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Strong Acid ◽  
Similar Type ◽  
Acid Media ◽  
Dicarbonyl Compounds

5,5-Dimethylcyclohexane-1,3-dione and its derivatives were shown to isomerize to give 5,6-dihydropyran-4-ones on irradiation in FSO3H or 98% H2SO4. The 2,2-dimethyl derivative, lacking hydrogen on C2, failed to give any products under the same conditions. A similar type of isomerization was also observed with thiolane-2,4-dione and its derivatives, while no photoisomerization was observed with their nitrogen or oxygen analogs. A possible reaction mechanism is proposed.

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.

Organocatalytic Group Transfer Reactions with Hypervalent Iodine­ Reagents

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 359-370 ◽  
Author(s):  
Marcin Kalek ◽  
Manoj Ghosh ◽  
Adam Rajkiewicz
Keyword(s):  
Short Review ◽  
Lewis Base ◽  
Base Catalysis ◽  
Synthetic Methods ◽  
Hypervalent Iodine ◽  
Group Transfer ◽  
Iodine Compounds ◽  
Amine Catalysis ◽  
Brønsted Base ◽  
Brønsted And Lewis Acid

In recent years, a plethora of synthetic methods that employ hypervalent iodine compounds donating an atom or a group of atoms to an acceptor molecule have been developed. Several of these transformations utilize organocatalysis, which complements well the economic and environmental advantages offered by iodine reagents. This short review provides a systematic survey of the organocatalytic approaches that have been used to promote group transfer from hypervalent iodine species. It covers both the reactions in which an organocatalyst is applied to activate the acceptor, as well as those that exploit the organocatalytic activation of the hypervalent iodine reagent itself.1 Introduction2 Organocatalytic Activation of Acceptor2.1 Amine Catalysis via Enamine and Unsaturated Iminium Formation2.2 NHC Catalysis via Acyl Anion Equivalent and Enolate Formation2.3 Chiral Cation Directed Catalysis and Brønsted Base Catalysis via Pairing with Stabilized Enolates3 Organocatalytic Activation of Hypervalent Iodine Reagent3.1 Brønsted and Lewis Acid Catalysis3.2 Lewis Base Catalysis3.3 Radical Reactions with Organic Promoters and Catalysts4 Summary and Outlook

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