Oxidative halogenation of aromatic compounds in the Pb3O4-Hal?-CF3CO2H system

Makhon'kov, D. I.; Cheprakov, Andrei V.; Rodkin, Mikhail A.; Serguchev, Yu. A.; Davydova, V. G.; Beletskaya, I. P.

doi:10.1007/bf00957338

Cited by 3 publications

(5 citation statements)

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“…In many cases an intermediately formed and highly reactive trifluoroacetyl hypoiodite is postulated as the iodinating species [5,11,29,30]. The existence of this in situ formed iodination agent was indeed confirmed by n.m.r.…”

Section: Iodinating Speciesmentioning

confidence: 88%

“…This species was first postulated in 1952 by Haszeldine and Sharp in the reaction of silver trifluoroacetate and iodine in nitrobenzene [11]. Recently a Russian group studied the direct iodination of monosubstituted arenes in the presence of cobalt(III) acetate, manganese(III) acetate and ammonium cerium(IV) sulfate in TFA and also postulated trifluoroacetyl hypoiodite as the actual iodinating agent, formed according to following equation [5]:…”

Section: Iodinating Speciesmentioning

confidence: 99%

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Direct n.c.a. radioiodination of weakly activated arenes using metal salts

Mennicke¹,

Holschbach²,

Coenen

2000

Radiochimica Acta

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Section: Iodinating Speciesmentioning

confidence: 88%

Section: Iodinating Speciesmentioning

confidence: 99%

Direct n.c.a. radioiodination of weakly activated arenes using metal salts

Mennicke¹,

Holschbach²,

Coenen

2000

Radiochimica Acta

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“…To circumvent the extreme hygroscopicity of Pb(OAc) 4 , its perfluorinated analogue can be formed in situ from Pb 3 O 4 and trifluoroacetic acid. This method was found to be less prone to side reactions, when compared to using Pb(OAc) 4 directly [167] …”

Section: Lead Tetraacetatementioning

confidence: 99%

“…Lead Tetraacetate Lead tetraacetate Pb(OAc) 4 is capable of oxidising bromides to bromine, which can then be used to brominate double and triple bonds, [166] and aromatic substrates. [167] To circumvent the extreme hygroscopicity of Pb(OAc) 4 , its perfluorinated analogue can be formed in situ from Pb 3 O 4 and trifluoroacetic acid. This method was found to be less prone to side reactions, when compared to using Pb(OAc) 4 directly.…”

Section: Cerium Ammonium Nitrate (Can)mentioning

confidence: 99%

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Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

2022

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Bromination of organic substances is still an important reaction in modern synthetic chemistry. In view of the increasing demand for sustainable synthetic chemistry, oxidative bromination can play an important role to avoid the use of hazardous molecular bromine (Br 2 ). In this review, a complete overview of the chemical oxidants will be provided which have been used for the electrophilic as well as radical brominations, starting from less hazardous bromide Br(À I); e. g., HBr or a bromide salt, with a focus on the differences caused by the choice of oxidant.

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Oxidative transformation of aryls using molybdenum pentachloride

Waldvogel

Trosien

2012

Chem. Commun.

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Molybdenum pentachloride combines a strong Lewis acid character with an unusually high oxidation potential creating a powerful reagent for oxidative transformations. Since the oxidative coupling reaction of aryls is induced at an extraordinarily high reaction rate, a variety of labile groups, e.g. iodo, tert-alkyl, etc., are tolerated on the aromatic core. Furthermore, the co-formed molybdenum salts can either be exploited for template effects to obtain uncommon geometries in a preferred manner, or redox-play starts after aqueous workup. Therefore MoCl(5) represents a unique and easily available reagent.

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Oxidative halogenation of aromatic compounds in the Pb3O4-Hal?-CF3CO2H system

Cited by 3 publications

References 1 publication

Direct n.c.a. radioiodination of weakly activated arenes using metal salts

Direct n.c.a. radioiodination of weakly activated arenes using metal salts

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

Oxidative transformation of aryls using molybdenum pentachloride

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