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

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 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.

Language: Английский

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Diastereodivergent nucleophile–nucleophile alkene chlorofluorination

Nature Chemistry, Journal Year: 2024, Volume and Issue: 16(10), P. 1647 - 1655

Published: July 1, 2024

The selective hetero-dihalogenation of alkenes provides useful building blocks for a broad range chemical applications. Unlike homo-dihalogenation, reactions, especially fluorohalogenation, are underdeveloped. Current approaches combine an electrophilic halogen source with nucleophilic source, which necessarily leads to anti-addition, and regioselectivity has only been achieved using highly activated alkenes. Here we describe alternative, nucleophile-nucleophile approach that adds chloride fluoride ions over unactivated in regio-, chemo- diastereoselective manner. A curious switch the reaction mechanism was discovered, triggers complete reversal diastereoselectivity promote either anti- or syn-addition. conditions demonstrated on array pharmaceutically relevant compounds, detailed mechanistic studies reveal selectivity between syn- anti-diastereomers based different active iodanes two halides first.

Language: Английский

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A decade of lessons in the activation of ArIL₂ species

Chemical Science, Journal Year: 2024, Volume and Issue: 15(11), P. 3784 - 3799

Published: Jan. 1, 2024

Developments in methods to increase the oxidative capacity of ArIL 2 reagents are discussed, with a focus on an understanding these species' behaviour from perspective iodine.

Language: Английский

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Photoredox synthesis of Vicinal Dichloride using FeCl₃ as chlorine source

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(6)

Published: May 2, 2023

Abstract This work presents a photo‐redox vicinal dichlorination of acrylamides using naturally abundant chlorine source (FeCl 3 ). The LMCT FeCl is responsible for the radical inducement, while tetra‐ n ‐butylammonium decatungstate (TBADT) catalytic system enhanced process. method exhibits extraordinarily mild conditions, not requiring external ligands and low E factors, which enables scalable synthesis.

Language: Английский

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Visible-light-induced controllable α-chlorination of nafimidone derivatives through LMCT excitation of CuCl2

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 537, P. 112950 - 112950

Published: Jan. 24, 2023

Language: Английский

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

Dalton Transactions, Journal Year: 2022, Volume and Issue: 51(32), P. 12384 - 12388

Published: Jan. 1, 2022

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

Language: Английский

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