Electrophilic activation of molecular bromine mediated by I(iii) DOI
Lachlan Sharp‐Bucknall,

Tania Tania,

Marcus Sceney

et al.

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(44), P. 16472 - 16479

Published: Jan. 1, 2023

In pursuit of a genuine bromo-λ3-iodane, it has been found that the combination Br2 and electron deficient λ3-iodanes can result in delivery both bromine atoms from to range aryl substrates, some highly deactivated. These brominations occur rapidly common chlorinated solvents at room temperature be achieved with catalytic activation commercially available PhI(OAc)2 PhI(OTFA)2. para-NO2 substituted derivatives are employed direct bromination towards more deactivated substrates. The mechanism is discussed insights being made, however remains unclear.

Language: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

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

Citations

28
A decade of lessons in the activation of ArIL2 species DOI Creative Commons

Tania Tania,

Marcus Sceney, Jason L. Dutton

et al.

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

Citations

2
Synthesis, structural characterization, reactivity and catalytic activity of mixed halo/triflate ArI(OTf)(X) species DOI
Lachlan Sharp‐Bucknall, Marcus Sceney, Keith F. White

et al.

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(11), P. 3358 - 3370

Published: Jan. 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.

Language: Английский

Citations

5
Electrophilic activation of molecular bromine mediated by I(iii) DOI
Lachlan Sharp‐Bucknall,

Tania Tania,

Marcus Sceney

et al.

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(44), P. 16472 - 16479

Published: Jan. 1, 2023

In pursuit of a genuine bromo-λ3-iodane, it has been found that the combination Br2 and electron deficient λ3-iodanes can result in delivery both bromine atoms from to range aryl substrates, some highly deactivated. These brominations occur rapidly common chlorinated solvents at room temperature be achieved with catalytic activation commercially available PhI(OAc)2 PhI(OTFA)2. para-NO2 substituted derivatives are employed direct bromination towards more deactivated substrates. The mechanism is discussed insights being made, however remains unclear.

Language: Английский

Citations

2