Cobalt(II) acetylacetonate catalyzed Friedel–Crafts acylation of anisole, thioanisole, and toluene

Tamilselvan, Pitchiah; Basavaraju, Y. B.; Murugesan, Ramachandran; Sampathkumar, Ellappan

doi:10.1016/j.catcom.2008.09.025

Cited by 9 publications

(5 citation statements)

References 16 publications

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“…At this juncture, the studies on preparation, characterization and catalytic application of metal acetylacetonate anchored onto porous supports have been under intensive investigation [15][16][17][18][19][20]. In one of our recent reports, Fe(III) acetylacetonate containing salen anchored SBA-15 catalyst has been prepared [21] and found that it is an efficient solid catalyst for the oxidative cleavage of C=C bond of styrene and its derivatives into corresponding carbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

Oxidative Cleavage of C=C Bond of Styrene and Its Derivatives with H2O2 using Vanadyl (IV) Acetylacetonate Anchored SBA-15 Catalyst

et al. 2011

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Section: Introductionmentioning

confidence: 99%

Oxidative Cleavage of C=C Bond of Styrene and Its Derivatives with H2O2 using Vanadyl (IV) Acetylacetonate Anchored SBA-15 Catalyst

et al. 2011

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“…1-(4-(Methylthio)phenyl)propan-1-one (S1j). 33 Prepared according to route A. 1 H NMR: (400.0 MHz, CDCl 3 ): δ 7.90−7.86 (m, 2H), 7.26−7.24 (m, 2H), 2.96 (q, J = 7.2 Hz, 2H), 2.52 (s, 3H), 1.22 (t, J = 7.2 Hz, 3H).…”

Section: ■ Conclusionmentioning

confidence: 99%

Cobalt-CatalyzedE-Selective Isomerization of Alkenes with a Phosphine-Amido-Oxazoline Ligand

Cai

Ding

et al. 2020

ACS Omega

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An efficient method to access (E)-trisubstituted alkenes is reported via cobalt-catalyzed isomerization of 1,1-disubstituted alkenes using a phosphine-amido-oxazoline ligand. The reaction could also convert mono- and 1,2-disubstituted alkenes to (E)-internal alkenes with benzylic selectivity. This protocol is atom-economy and operationally simple and uses readily available starting materials with good functional tolerance. This catalytic system could be scaled up to gram scale smoothly with a catalyst loading of 0.1 mol %.

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“…The reaction was quenched with hydrogen chloride (aqueous or gaseous) that provided the racemic hydrochloride mephedrone salt. A Friedel‐Crafts acylation route, starting with toluene and propanoyl chloride in the presence of a suitable Lewis acid as a catalyst, may also be used to produce the 4‐methylpropiophenone intermediate . Another potential route to mephedrone synthesis involves the oxidation of 4‐methylephedrine in a simple one‐step reaction process or a Grignard reaction using 4‐methylbenzaldehyde as the starting material …”

Section: Introductionmentioning

confidence: 99%

“…A Friedel-Crafts acylation route, starting with toluene and propanoyl chloride in the presence of a suitable Lewis acid as a catalyst, may also be used to produce the 4-methylpropiophenone intermediate. [7] Another potential route to mephedrone synthesis involves the oxidation of 4-methylephedrine in a simple one-step reaction process or a Grignard reaction using 4-methylbenzaldehyde as the starting material. [8] Detailed published information on possible synthetic mephedrone impurities and route-specific by-products are currently unavailable, although it has been recognized that the formation of iso-cathinones may be relevant for the chemistry of synthetic cathinones.…”

Section: Introductionmentioning

confidence: 99%

Identification and characterization of an imidazolium by‐product formed during the synthesis of 4‐methylmethcathinone (mephedrone)

Power

Kavanagh

McLaughlin

et al. 2015

Drug Testing and Analysis

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Abstract:Abstract 4-Methylmethcathinone (2-methylamino-1-(4-methylphenyl)propan-1-one, mephedrone) is a psychoactive substance that has been associated with recreational use worldwide. Analytical data related to mephedrone are abundantly available but the characterization of by-products obtained during organic synthesis remains to be explored. This study presents the identification of a 1,2,3,5-tetramethyl-4-(4-methylphenyl)-1H-imidazol-3-ium salt (TMMPI), which was formed during the synthesis of mephedrone. When diethyl ether was added to the crude reaction product, solid material precipitated from the solution. Analytical characterization of TMMPI employed a range of analytical techniques including chromatographic analysis in combination with various mass spectrometric detection methods, nuclear magnetic resonance spectroscopy and crystal structure analysis. Additional confirmation was obtained from organic synthesis of the imidazolium by-product. When TMMPI was subjected to analysis by gas chromatography-mass spectrometry (GC-MS), isomerization and degradation into two distinct compounds were observed, which pointed toward thermal instability under GC conditions. An LC-MS based investigation into a micro scale synthesis of mephedrone and three additional analogues revealed that the corresponding TMMPI analogue was formed. Interestingly, storage of mephedrone freebase in a number of http://mc.manuscriptcentral.com/dta Drug Testing and AnalysisAccepted but uncorrected F o r P e e r R e v i e w organic solvents also gave rise to TMMPI and it appeared that its formation during storage was significantly reduced in the absence of air. The present study was aimed to support clandestine forensic investigations by employing analytical strategies that are applicable to manufacturing sites. The imidazolium salts will most likely be found amongst the waste products of any clandestine lab site under investigation rather than with the desired product. When TMMPI was subjected to analysis by gas chromatography-mass spectrometry (GC-MS), isomerization and degradation into two distinct compounds were observed, which pointed toward thermal instability under GC conditions. An LC-MS based investigation into a micro scale synthesis of mephedrone and three additional analogues revealed that the corresponding TMMPI analogue was formed.Interestingly, storage of mephedrone freebase in a number of organic solvents also gave rise to TMMPI and it appeared that its formation during storage was significantly reduced in the absence of air. The present study was aimed to support clandestine forensic investigations by employing analytical strategies that are applicable to manufacturing sites. The imidazolium salts will most likely be found amongst the waste products of any clandestine lab site under investigation rather than with the desired product.

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Cobalt(II) acetylacetonate catalyzed Friedel–Crafts acylation of anisole, thioanisole, and toluene

Cited by 9 publications

References 16 publications

Oxidative Cleavage of C=C Bond of Styrene and Its Derivatives with H2O2 using Vanadyl (IV) Acetylacetonate Anchored SBA-15 Catalyst

Oxidative Cleavage of C=C Bond of Styrene and Its Derivatives with H2O2 using Vanadyl (IV) Acetylacetonate Anchored SBA-15 Catalyst

Cobalt-CatalyzedE-Selective Isomerization of Alkenes with a Phosphine-Amido-Oxazoline Ligand

Identification and characterization of an imidazolium by‐product formed during the synthesis of 4‐methylmethcathinone (mephedrone)

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