Oxidative Monofluorination of 1,4-Diiodo(or Dibromo)-2,3,5,6-tetramethylbenzenes in the System PbO₂—HF—Py—CH₂Cl₂

The oxidation of 1,4-diiodo-2,3,5,6-tetramethylbenzene (diiododurene) and 1,4-dibromo-2,3,5,6-tetramethylbenzene (dibromodurene) by lead dioxide PbO₂ in Olah reagent, hydrogen fluoride-pyridine mixture, with CH₂Cl₂ as a co-solvent at room temperature for 96 h results in the corresponding products of monofluorination of methyl group. This is the first example of using the oxidative system PbO₂—HF—Py—CH₂Cl₂ for side-chain monofluorination of methylated benzenes.

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Journal
Журнал органической химии
Published
2024-12-27
DOI
https://doi.org/10.31857/s0514749224020011
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Oxidative Monofluorination of 1,4-Diiodo(or Dibromo)-2,3,5,6-tetramethylbenzenes in the System PbO₂—HF—Py—CH₂Cl₂

Aleksander V. Vasilyev, Mikhail V. Kalyaev, Dmitry S. Ryabukhin
Журнал органической химии
Fluorine in Organic Chemistry
article

Oxidative Monofluorination of 1,4-Diiodo(or Dibromo)-2,3,5,6-tetramethylbenzenes in the System PbO₂—HF—Py—CH₂Cl₂

Aleksander V. Vasilyev, Mikhail V. Kalyaev, Dmitry S. Ryabukhin
article en

Abstract

The oxidation of 1,4-diiodo-2,3,5,6-tetramethylbenzene (diiododurene) and 1,4-dibromo-2,3,5,6-tetramethylbenzene (dibromodurene) by lead dioxide PbO₂ in Olah reagent, hydrogen fluoride-pyridine mixture, with CH₂Cl₂ as a co-solvent at room temperature for 96 h results in the corresponding products of monofluorination of methyl group. This is the first example of using the oxidative system PbO₂—HF—Py—CH₂Cl₂ for side-chain monofluorination of methylated benzenes.

Журнал органической химииVol. 60(2-3)
St Petersburg University (RU), All-Russian Scientific Research Institute of Refrigeration Industry (RU), Saint Petersburg State Forest Technical University (RU)
Clean water and sanitation
Openalex Percentile: Top 81%
Fluorine in Organic Chemistry
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Oxidative Monofluorination of 1,4-Diiodo(or Dibromo)-2,3,5,6-tetramethylbenzenes in the System PbO₂—HF—Py—CH₂Cl₂ — Aleksander V. Vasilyev, Mikhail V. Kalyaev, et al. · Журнал органической химии (2024) | TGRS Research Map | TGRS