Synthesis of pyridines with fluoro-containing superlipophilic substituents

Sipyagin, A. M.; Помыткин, И. А.; Pal'tsun, S. V.; Aleinikov, N. N.; Карцев, В. Г.

doi:10.1016/s0022-1139(00)83625-8

Cited by 15 publications

(5 citation statements)

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“…However, only two reports are related to the preparation of SF 5 ‐substituted pyridines. The synthesis of 4‐SF 5 ‐2,3,5,6‐tetrachloropyridine was briefly reported in 30–40 % yield by heating the corresponding thiol with IF 5 but no experimental or characterization details were provided 7a. The second report is a patent describing the synthesis of 2‐SF 5 ‐pyridine by oxidative fluorination of 2,2′‐dipyridyl disulfide with the strong oxidizing fluorinating reagent AgF 2 in nonane for 5 hours at 120 °C 7b.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of 2‐Pyridylsulfur Pentafluorides

Kanishchev

Dolbier

2014

Angew Chem Int Ed

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Current approaches to prepare SF5 -substituted heterocycles during the synthesis of targeted heterocyclic compounds require the use of SF5 -functionalized aryl or alkyne reagents or SF5 Cl as a source of the SF5 functional group. Herein we report that excess oxidative fluorination of 2,2'-dipyridyl disulfide with a KF/Cl2 /MeCN system leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides (2-SF4 Cl-pyridines). These molecules are found to undergo further chlorine-fluorine exchange reactions by treatment with silver(I) fluoride enabling ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides (2-SF5 -pyridines). This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5 -substituted heterocycles.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of 2‐Pyridylsulfur Pentafluorides

Kanishchev

Dolbier

2014

Angew Chem Int Ed

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“…Another direct oxidation procedure was developed by Karstev and co‐workers (Scheme 27), [70] who synthesized polychloropyridine‐SF 5 132 by the direct oxidation of the corresponding thiols 131 with IF 5 . However, this procedure also suffered from low yields and narrow scope.…”

Section: Fluorination Levelmentioning

confidence: 99%

“…Although low yields were obtained in all cases, this pioneering study from Sheppard et al opened a new pathway in the synthesis or arylsulfur(VI) fluorides [69] and the further application to several fields such as biology and medicinal chemistry. [11] Another direct oxidation procedure was developed by Karstev and co-workers (Scheme 27), [70] who synthesized polychloropyridine-SF 5 132 by the direct oxidation of the corresponding thiols 131 with IF 5 . However, this procedure also suffered from low yields and narrow scope.…”

Section: Direct Oxidation Of Diaryldisulfides or Arylthiolsmentioning

confidence: 99%

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(Hetero)aryl‐S^VI Fluorides: Synthetic Development and Opportunities

Magre

Cornellà

2022

Angewandte Chemie

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Hetero)arylsulfur compounds where the S atom is in the oxidation state VI represent a large percentage of the molecular functionalities present in organic chemistry. More specifically, (hetero)aryl-S VI fluorides have recently received enormous attention because of their potential as chemical biology probes, as a result of their reactivity in a simple, modular, and efficient manner. Whereas the synthesis and application of the level 1 fluorination at S VI atoms (sulfonyl and sulfonimidoyl fluorides) have been widely studied and reviewed, the synthetic strategies towards higher levels of fluorination (levels 2 to 5) are somewhat more limited. This Minireview evaluates and summarizes the progress in the synthesis of highly fluorinated aryl-S VI compounds at all levels, discussing synthetic strategies, reactivity, the advantages and disadvantages of the synthetic procedures, the proposed mechanisms, and the potential upcoming opportunities.

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“…Nevertheless, Sipyagin et al, have employed this method for the perfluoroalkylation of thiols such as polychloropyridine thiols [221]. Two different methods were used: the action of preformed xenon carboxylates (method A) or treatment of a pyridinethiol solution in R F COOH directly with xenon difluoride (method B).…”

Section: Reviewmentioning

confidence: 99%

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

Boiko¹

2010

Beilstein J. Org. Chem.

260

119

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SummaryThis review covers all of the common methods for the syntheses of aromatic and heterocyclic perfluoroalkyl sulfides, a class of compounds which is finding increasing application as starting materials for the preparation of agrochemicals, pharmaceutical products and, more generally, fine chemicals. A systematic approach is taken depending on the mode of incorporation of the SRF groups and also on the type of reagents used.

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Synthesis of pyridines with fluoro-containing superlipophilic substituents

Cited by 15 publications

References 0 publications

Synthesis and Characterization of 2‐Pyridylsulfur Pentafluorides

Synthesis and Characterization of 2‐Pyridylsulfur Pentafluorides

(Hetero)aryl‐S^VI Fluorides: Synthetic Development and Opportunities

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

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Synthesis of pyridines with fluoro-containing superlipophilic substituents

Cited by 15 publications

References 0 publications

Synthesis and Characterization of 2‐Pyridylsulfur Pentafluorides

Synthesis and Characterization of 2‐Pyridylsulfur Pentafluorides

(Hetero)aryl‐SVI Fluorides: Synthetic Development and Opportunities

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

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(Hetero)aryl‐S^VI Fluorides: Synthetic Development and Opportunities