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
Процитировано
34Sustainable and scalable one-pot synthesis of diaryliodonium salts
Chemical Communications, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
Two one-pot syntheses of diaryliodonium triflates are presented, rendering the production these electrophilic arylating agents more sustainable.
Язык: Английский
Процитировано
1Transition-Metal-Free C-Diarylations to Reach All-Carbon Quaternary Centers
JACS Au, Год журнала: 2024, Номер 4(8), С. 2832 - 2837
Опубликована: Авг. 5, 2024
Herein, we disclose a convenient protocol for the α-diarylation of carbon nucleophiles to yield heavily functionalized quaternary products. Diaryliodonium salts are utilized transfer both aryl groups under transition-metal-free conditions, which enables an atom-efficient and high-yielding method with broad functional group tolerance. The methodology is amenable wide variety can be in late-stage functionalization complex arenes. Furthermore, it compatible new class zwitterionic iodonium reagents, gives access phenols
Язык: Английский
Процитировано
4Synthesis of Versatile Aryliodine Synthons by Aryliodonium Rearrangement Reactions
Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(7)
Опубликована: Май 9, 2024
Abstract The excellent reactivity of diaryliodonium salts has primarily been attributed to the efficient departure iodoarene unit, facilitating a variety arylation reactions. However, one equivalent as side‐product is chemical waste in these reactions, which was criticized by chemists for hindering its popularity. Recently, development synthetic methodology that preserve aryl iodine moiety received increasing attention. Oxidative rearrangement reactions involving aryliodonium reagents have significantly addressed atom‐economic issue, thereby broadening reaction scope. resulting intricate aryliodine products are viewed valuable synthons synthesis natural products, pharmaceutical intermediates and other fine chemicals.
Язык: Английский
Процитировано
3Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations
Chemical Reviews, Год журнала: 2025, Номер unknown
Опубликована: Март 7, 2025
Constructing chemical bonds under green sustainable conditions has drawn attention from environmental and economic perspectives. The dissociation of (hetero)aryl-halide is a crucial step most arylations affording (hetero)arene derivatives. Herein, we summarize the (hetero)aryl halides activation enabling direct (hetero)arylation trapping reagents construction highly functionalized (hetero)arenes benign conditions. strategies for aryl iodides are classified into (a) hypervalent iodoarene followed by functionalization thermal/photochemical conditions, (b) aryl-I bond in presence bases with/without organic catalysts promoters, (c) photoinduced presence/absence organophotocatalysts, (d) electrochemical direct/indirect electrolysis mediated organocatalysts mediators acting as electron shuttles, (e) electrophotochemical redox-active organocatalysts. These modes result exhibiting diverse reactivity formal cations/radicals/anions aryne precursors. coupling these reactive intermediates with leads to facile selective formation C-C C-heteroatom bonds. ecofriendly, inexpensive, functional group-tolerant offer alternatives transition metal-based catalysis.
Язык: Английский
Процитировано
0Ortho-Hydroxy-Substituted Diaryliodonium Salts Enabled Intramolecular Aryliodonium Rearrangement in Synthesis of Ortho-Iodo Diaryl Ethers
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Апрель 15, 2025
A new family of ortho-hydroxy-substituted diaryliodonium salts was synthesized with 1-acetoxy-2-iodobenzenes, in which the acetyl group cleaved a one-pot synthesis. The ortho-hydroxyl-substituted underwent further intramolecular aryl migration reaction, giving ortho-iodo diaryl ethers either or without presence bases.
Язык: Английский
Процитировано
0Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins
Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 841 - 851
Опубликована: Апрель 18, 2024
Cyclic annulation involving diaryliodonium salts is an efficient tool for the construction of two or more chemical bonds in a one-pot process.
Язык: Английский
Процитировано
2Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts
Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2891 - 2920
Опубликована: Ноя. 13, 2024
Diaryliodonium salts have become widely recognized as arylating agents in the last two decades. Both, symmetrical and unsymmetrical forms of these serve effective electrophilic reagents various organic syntheses. The use diaryliodoniums C–C carbon–heteroatom bond formations, particularly under metal-free conditions, has further enhanced popularity reagents. In this review, we concentrate on arylation reactions involving carbon other heteroatoms, encompassing rearrangement absence any metal catalyst, summarize advancements made five years.
Язык: Английский
Процитировано
2Coplanar Atropochiral 5H‐Cyclopenta[2,1‐b:3,4‐b']dipyridine Ligands: Synthesis and Applications in Asymmetric Ring‐Opening Reaction
Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown
Опубликована: Окт. 8, 2024
Abstract Bipyridines represent a class of ligands renowned for their versatility and efficacy in numerous transition metal‐catalyzed reactions. Chiral bipyridine are noted distinctive reactivity stereoselectivity. In this work, we have designed synthesized endowed with an axially chiral scaffold. These feature: (a) precisely aligned coplanar framework that is beneficial metal chelation; (b) spacious environment around the metal‐bipyridine complexes, capable hosting substrates substantial steric bulk; (c) pocket induced by architecture. atropochiral planar were successfully applied copper‐catalyzed ring‐opening reactions cyclic diaryliodoniums bulky secondary amines, achieving high efficiency stereoselectivity unsuccessful our previous efforts.
Язык: Английский
Процитировано
1Metal-Free Synthesis of Benzisoxazolones Utilizing ortho-Ester and ortho-Cyano-Functionalized Diaryliodonium Salts with Protected Hydroxylamines
The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Ноя. 10, 2024
Herein, we report the development of metal-free one/two-pot procedures for synthesis benzo[
Язык: Английский
Процитировано
1