2,4,6-Tris(4-iodophenoxy)-1,3,5-triazine as a new recyclable “iodoarene” for in situ generation of hypervalent iodine(III) reagent for α-tosyloxylation of enolizable ketones

2014 ◽  
Vol 55 (22) ◽  
pp. 3332-3335 ◽  
Author(s):  
Prerana B. Thorat ◽  
Bhagyashree Y. Bhong ◽  
Amol V. Shelke ◽  
Nandkishor N. Karade
Keyword(s):  
Hypervalent Iodine ◽  
In Situ Generation

Hypervalent iodine catalysis for selective oxidation of Baylis–Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone

2016 ◽  
Vol 40 (12) ◽  
pp. 10300-10304 ◽  
Author(s):  
Raktani Bikshapathi ◽  
Parvathaneni Sai Prathima ◽  
Vaidya Jayathirtha Rao
Keyword(s):  
Selective Oxidation ◽  
Carbonyl Compounds ◽  
Hypervalent Iodine ◽  
In Situ Generation ◽  
Iodosobenzoic Acid ◽  
High Yields

An efficient, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds in high yields has been developed with 2-iodosobenzoic acid (IBA).

An I(I)/I(III) Catalysis Route to the Heptafluoroisopropyl Group: A Privileged Module in Contemporary Agrochemistry

Synthesis ◽  
2021 ◽  
Author(s):  
Victor Martín-Heras ◽  
Constantin G. Daniliuc ◽  
Ryan Gilmour
Keyword(s):  
Functional Groups ◽  
Hypervalent Iodine ◽  
Aryl Ring ◽  
Iodine Species ◽  
Single Operation ◽  
Group A ◽  
Molecule Design ◽  
In Situ Generation

The heptafluoroisopropyl group is emerging as a privileged chemotype in contemporary agrochemistry and features prominently in the current portfolio of leading insecticides. To reconcile the expansive potential of this module with the synthetic challenges associated with preparing crowded, fluorinated motifs, I(I)/I(III) catalysis has been leveraged. Predicated on in situ generation of p-TolIF2, this route enables the direct difluorination of α-trifluoromethyl-β-difluoro-styrenes in a single operation. This formal addition of fluorine across the alkene π-bond is efficient (up to 91%) and is compatible with a broad range of functional groups. The ArCF(CF3)2 moiety is conformationally pre-organized, with the C(sp3)-F bond co-planar to the framework of the aryl ring, thereby minimizing 1,3-allylic strain. Moreover, orthogonal multipolar C-F•••C=O interactions have been identified in a phathalimide derivative. It is envisaged that this programmed vicinal difluorination enabled by a hypervalent iodine species will find application in functional molecule design in a broader sense.

scholarly journals Cover Feature: In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes (Eur. J. Org. Chem. 17/2019)

2019 ◽  
Vol 2019 (17) ◽  
pp. 2768-2768
Author(s):  
Albert Granados ◽  
Zhiyu Jia ◽  
Marc del Olmo ◽  
Adelina Vallribera
Keyword(s):  
Hypervalent Iodine ◽  
In Situ Generation

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.

Direct Cyanation of Heteroaromatic Compounds Mediated by Hypervalent Iodine(III) Reagents:  In Situ Generation of PhI(III)−CN Species and Their Cyano Transfer

2007 ◽  
Vol 72 (1) ◽  
pp. 109-116 ◽  
Author(s):  
Toshifumi Dohi ◽  
Koji Morimoto ◽  
Naoko Takenaga ◽  
Akihiro Goto ◽  
Akinobu Maruyama ◽  
...  
Keyword(s):  
Hypervalent Iodine ◽  
Heteroaromatic Compounds ◽  
In Situ Generation

scholarly journals Direct Cyanation of Heteroaromatic Compounds Mediated by Hypervalent Iodine(III) Reagents: In situ Generation of PhI(III)—CN Species and Their Cyano Transfer.

ChemInform ◽  
2007 ◽  
Vol 38 (19) ◽  
Author(s):  
Toshifumi Dohi ◽  
Koji Morimoto ◽  
Naoko Takenaga ◽  
Akihiro Goto ◽  
Akinobu Maruyama ◽  
...  
Keyword(s):  
Hypervalent Iodine ◽  
Heteroaromatic Compounds ◽  
In Situ Generation

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

2019 ◽  
Vol 2019 (17) ◽  
pp. 2812-2818 ◽  
Author(s):  
Albert Granados ◽  
Zhiyu Jia ◽  
Marc del Olmo ◽  
Adelina Vallribera
Keyword(s):  
Hypervalent Iodine ◽  
In Situ Generation

Highly diastereo- and enantioselective organocatalytic synthesis of trifluoromethylated erythritols based on the in situ generation of unstable trifluoroacetaldehyde

2021 ◽  
Author(s):  
Kazumasa Funabiki ◽  
Toshiya Gotoh ◽  
Ryunosuke Kani ◽  
Toshiyasu Inuzuka ◽  
Yasuhiro Kubota
Keyword(s):  
Trifluoromethyl Group ◽  
In Situ Generation

A highly diastereo- and enantioselective organocatalytic method to synthesise erythritols bearing a trifluoromethyl group has been investigated.

Recent advances in Minisci-type reactions and applications in organic synthesis

2020 ◽  
Vol 24 ◽  
Author(s):  
Wengui Wang ◽  
Shoufeng Wang
Keyword(s):  
Free Radical ◽  
Hydrogen Atom ◽  
Organic Synthesis ◽  
Radical Reactivity ◽  
Atom Loss ◽  
Radical Generation ◽  
In Situ Generation ◽  
Thermal Cleavage ◽  
Synthetic Chemist

Abstract:: Minisci-type reactions have become widely known as reactions that involve the addition of carbon-centered radicals to basic heteroarenes followed by formal hydrogen atom loss. While the originally developed protocols for radical generation remain in active use today, in recent years by a new array of radical generation strategies allow use of a wider variety of radical precursors that often operate under milder and more benign conditions. New transformations based on free radical reactivity are now available to a synthetic chemist looking to utilize a Minisci-type reaction. Radical-generation methods based on photoredox catalysis and electrochemistry, which utilize thermal cleavage or the in situ generation of reactive radical precursors, have become popular approaches. Our review will cover the remarkably literature that has appeared on this topic in recent 5 years, from 2015-01 to 2020-01, in an attempt to provide guidance to the synthetic chemist, on both the challenges that have been overcome and applications in organic synthesis.

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