Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Chemical Reviews, Год журнала: 2024, Номер unknown

Опубликована: Сен. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Язык: Английский

---

Synthesis, structural characterization, reactivity and catalytic activity of mixed halo/triflate ArI(OTf)(X) species

Dalton Transactions, Год журнала: 2023, Номер 52(11), С. 3358 - 3370

Опубликована: Янв. 1, 2023

Both mixed λ3-iodoarenes and possessing -OTf ligands are coveted for their enhanced reactivities. Here we describe the synthesis, reactivity, comprehensive characterisation of two new ArI(OTf)(X) species, a class compound that were previously only invoked as reactive intermediates where X = Cl, F divergent reactivity with aryl substrates. A catalytic system electrophilic chlorination deactivated arenes using Cl2 chlorine source ArI/HOTf catalyst is also described.

Язык: Английский

---

On the potential intermediacy of PhIBr₂ as a brominating agent

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(43), С. 8454 - 8460

Опубликована: Янв. 1, 2022

PhIBr 2 has been invoked as a brominating agent, however does not appear to exist but rather forms PhI and Br , with being responsible for bromination.

Язык: Английский

---

Gas-phase ion chemistry of [B12X12]2− (X = F, Cl, Br, I, CN). A brief review of twelve years of researching twelve−vertexed dianions and their fragments

International Journal of Mass Spectrometry, Год журнала: 2023, Номер 496, С. 117169 - 117169

Опубликована: Ноя. 19, 2023

Язык: Английский

---

Novel Chlorination of Imidazo‐Fused Heterocycles via Dichloro(aryl)‐λ³‐iodanes

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(30)

Опубликована: Июль 12, 2022

Abstract A novel, safe, convenient and efficient protocol has been developed for regioselective chlorination of imidazo‐fused heterocycles with dichloro(4‐(trifluoromethyl)phenyl)‐λ 3 ‐iodanes under mild conditions. The present approach avoids the need toxic chlorinating reagents, strong stoichiometric oxidants, metal catalysts or harsh reaction 36 examples heterocycle substrates were investigated, chlorinated products obtained moderate to excellent yields. Control experiments indicated that proceeded through an electrophilic aromatic substitution.

Язык: Английский

---

PhICl₂ is activated by chloride ions

Dalton Transactions, Год журнала: 2021, Номер 50(34), С. 11986 - 11991

Опубликована: Янв. 1, 2021

A study on the potential activating role of pyridine in electrophilic chlorination anisole by PhICl 2 has led to discovery that soluble sources chloride ions activate reaction at catalytic loadings, greatly increasing rate chlorination.

Язык: Английский

---

Catalytic role of amines in activation of PhICl₂ from a computational point of view

Chemical Communications, Год журнала: 2021, Номер 57(72), С. 9108 - 9111

Опубликована: Янв. 1, 2021

We thoroughly investigated mechanistic features of dichlorination diazoacetates using PhICl 2 catalysed by pyridine.

Язык: Английский

---

Kinetic study on the activation of PhICl₂ with Lewis bases for aromatic chlorination

Dalton Transactions, Год журнала: 2022, Номер 51(32), С. 12384 - 12388

Опубликована: Янв. 1, 2022

A kinetic study on the chlorination of arenes with nucleophilically activated PhICl 2 experimentally demonstrates nucleophile induces elimination chlorine gas.

Язык: Английский

---

Synthesis and Conformational Analysis of α,β‐Dichlorocarbonyl Compounds

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Авг. 21, 2024

Abstract α,β‐Dichlorocarbonyl compounds were synthesized by facile dichlorination of α,β‐unsaturated amides with TCIA‐PPh 3 and the resultant converted to ketones. Conformational analyses products performed confirm our previous hypothesis regarding vicinal dichlorinated carbonyl compounds. The exhibited 1 H NMR signals large coupling constants (7–11 Hz) for 1,2‐ anti ‐configuration small (3–4 syn ‐configuration. ‐pentane interaction enabled rational conformational analysis α,β‐dichlorinated compounds, although some interesting exceptions observed. Consideration these conformations is helpful in assigning relative configurations α,β‐dihalogenated general.

Язык: Английский

---

Derivatization of Undecahalogenated closo-Dodecaborates [B₁₂X₁₁NH₃]⁻ (X = F–I): Attaching Isocyanate, Amidinium, and Formamide Functionalities

Inorganic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 29, 2024

Halogenated

Язык: Английский

---