Synthesis of arylferrocenylketones

Rodríguez-Cendejas, Cristina G.; Liebeskind, Lanny S.; Peña‐Cabrera, Eduardo

doi:10.3998/ark.5550190.0006.621

Cited by 20 publications

(7 citation statements)

References 2 publications

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“…In an alternative approach, the closely related diethyl diester 14 was obtained by treatment of ferrocene‐1,1′‐bis(carbodioic acid) [76] ( 11 ) with oxalyl chloride affording acyl chloride 12 , which was not isolated but treated with ethanethiol giving thioester 13 in 93 % yield. Subsequent reaction with Lawesson's reagent [2,4‐bis(4‐methoxyphenyl)‐1,3,2,4‐dithiadiphosphetane‐2,4‐dithione] [77] gave diethyl bis(dithioate) 14 in 91 % yield (Scheme 4).…”

Section: Resultsmentioning

confidence: 99%

“…S , S ′ ‐Diethyl ferrocene‐1,1 ′ ‐bis(carbothioate) (13) : Pyridine (4 drops) and oxalyl chloride (0.15 mL, 1.8 mmol, 3.2 equiv.) were added dropwise to ferrocene‐1,1′‐dicarbocylic acid [76] ( 11 , 100 mg, 0.5 mmol, 1.0 equiv.) in dichloromethane (15 mL), and the mixture was heated at reflux (45 °C) for 2.5 h. After cooling to 23 °C the solvent was removed at reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

“…After solvent removal at reduced pressure, the crude product was purified by column chromatography (silica gel deactivated with triethylamine, 30 × 3 cm, petroleum ether!petroleum ether/ethyl acetate, 5 : 1) giving dimethyl ferrocene-1,1'-bis(carbodithioate) (10, 250 mg, 0.7 mmol, 25 %) as a dark red viscous oil. ) were added dropwise to ferrocene-1,1'-dicarbocylic acid [76] (11, 100 mg, 0.5 mmol, 1.0 equiv.) in dichloromethane (15 mL), and the mixture was heated at reflux (45°C) for 2.5 h. After cooling to 23°C the solvent was removed at reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

New π‐Extended 1,1′‐Disubstituted Ferrocenes with Thioate and Dithioate End Groups

Schmiel

Butenschön

2021

Eur J Org Chem

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Extended π systems based on 1,1′‐aryl or (2‐arylethynyl) disubstitution at ferrocene with thioate or dithioate end groups are reported. In the context of molecular electronics, such end groups are possible alternative end groups for the attachment of molecular wires at gold surfaces. The respective thioates were successfully prepared in high yields via the respective carboxylic acid derivatives. Subsequent treatment with Lawesson's reagent led to the respective dithioates. However, this did not work in the presence of triple bonds, in these cases, product mixtures were formed. On the basis of literature evidence with Woollin's reagent, the selenium analog of Lawesson's reagent, one product was tentatively characterized as a double cyclization product of two triple bonds and two molecules of Lawesson's reagent. Preliminary experiments towards the formation of gold complexes by reaction with a Johnphos gold(I) salt are included.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

New π‐Extended 1,1′‐Disubstituted Ferrocenes with Thioate and Dithioate End Groups

Schmiel

Butenschön

2021

Eur J Org Chem

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“…Ferrocenyl thioketones 8a-g were obtained by thionation of corresponding ferrocenyl ketones [29] by treatment with Lawesson's reagent [30]. Ferrocenyl β-naphthyl thioketone (8b) obtained from ferrocenyl(βnaphthyl) ketone [31] is reported for the first time (see Supporting Information File 1).…”

Section: Methodsmentioning

confidence: 99%

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

Mlostoń¹,

Kowalczyk²,

Augustin³

et al. 2020

Beilstein J. Org. Chem.

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Ferrocenyl thioketones reacted with donor–acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates reacted with the corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups were oriented in a cis-fashion. In contrast, the same cyclopropanes underwent reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. A low selectivity was also observed in the reaction of a 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone.

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“…Ferrocenyl β-naphthyl thioketone (8b) obtained from ferrocenyl(β-naphthyl) ketone [30] is reported for the first time (see SI).…”

Section: Methodsmentioning

confidence: 99%

Ferrocenyl-Substituted Tetrahydrothiophenes via Formal (3+2)-Cycloaddition Reactions of Ferrocenyl Thioketones With Donor-Acceptor Cyclopropanes

Mlostoń¹,

Kowalczyk²,

Augustin³

et al. 2020

Preprint

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Ferrocenyl thioketones react with donor-acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal (3+2)-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates react with corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups are oriented in a cis-fashion. In contrast, the same cyclopropanes undergo reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. Low selectivity was also observed in the reaction of 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone.

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Synthesis of arylferrocenylketones

Cited by 20 publications

References 2 publications

New π‐Extended 1,1′‐Disubstituted Ferrocenes with Thioate and Dithioate End Groups

New π‐Extended 1,1′‐Disubstituted Ferrocenes with Thioate and Dithioate End Groups

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

Ferrocenyl-Substituted Tetrahydrothiophenes via Formal (3+2)-Cycloaddition Reactions of Ferrocenyl Thioketones With Donor-Acceptor Cyclopropanes

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