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

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).

A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 630-634 ◽  
Author(s):  
Min Zhang ◽  
Jinling Su ◽  
Yan Zhang ◽  
Mingren Chen ◽  
Weiming Li ◽  
...  
Keyword(s):  
Metal Halide ◽  
Regioselective Synthesis ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Copper Halide ◽  
Experimental Conditions ◽  
Heteroaromatic Compounds ◽  
Convenient Approach ◽  
In Situ Generation

A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX2 alone or with ZnX2) promoted halogenation with N-halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X+) by the coordination of copper or zinc with the N-halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.

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.

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.

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