- A palladium-catalyzed C-H functionalization route to ketones: Via the oxidative coupling of arenes with carbon monoxide
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We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Exploiting the latter can also allow the synthesis of unsymmetrical ketones from two different arenes.
- Arndtsen, Bruce A.,Kinney, R. Garrison,Levesque, Taleah M.
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p. 3104 - 3109
(2020/03/27)
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- Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements
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The formation of fused pyrazoles via intramolecular 1,3-dipolar cycloadditions of diazo intermediates with pendant alkynes is described. A subsequent thermal [1s, 5s] sigmatropic shift of these pyrazole systems resulted in a ring contraction, forming spirocyclic pyrazoles. The limitations of this rearrangement were explored by changing the substituents on the nonmigrating aromatic ring and by using substrates lacking an aromatic linkage to the propargyl group.
- Dimirjian, Christine A.,Casti?eira Reis, Marta,Balmond, Edward I.,Turman, Nolan C.,Rodriguez, Elys P.,Di Maso, Michael J.,Fettinger, James C.,Tantillo, Dean J.,Shaw, Jared T.
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p. 7209 - 7212
(2019/10/02)
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- Synthesis of ketones via organolithium addition to acid chlorides using continuous flow chemistry
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An efficient method for the synthesis of ketones using organolithium and acid chlorides under continuous flow conditions has been developed. In contrast to standard batch chemistry, over-addition of the organolithium to the ketone for the formation of the undesired tertiary alcohol has been minimised representing a direct approach toward ketones.
- Moon, Soo-Yeon,Jung, Seo-Hee,Bin Kim,Kim, Won-Suk
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p. 79385 - 79390
(2015/10/06)
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- Dirhodium(II)-Catalyzed Cross-Coupling Reactions of Aryl Aldehydes with Arylboronic Acids in Water
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In this report, dirhodium(II) catalysts with axial phosphanes ligands were employed to catalyze cross-coupling reactions of aromatic aldehydes with arylboronic acids to generate ketones in neat water. The overall reaction is proposed to occur through a cascade process involving the dirhodium-catalyzed addition of boronic acids to aldehydes followed by the dehydrogenative oxidation of alcohols.
- Kuang, Yi,Wang, Yuanhua
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supporting information
p. 1163 - 1166
(2015/10/05)
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- Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids
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The first asymmetric insertion reactions of donor-donor carbenoids, i.e., those with no pendant electron-withdrawing groups, are reported. This process enables the synthesis of densely substituted benzodihydrofurans with high levels of enantio- and diaste
- Soldi, Cristian,Lamb, Kellan N.,Squitieri, Richard A.,Gonzlez-Lpez, Marcos,Di Maso, Michael J.,Shaw, Jared T.
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p. 15142 - 15145
(2015/02/19)
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- Pd-NHC-catalyzed synthesis of diaryl ketones
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With N-hetereocyclic carbene and palladium catalysis, diaryl ketones with a variety of functional groups that span from electron withdrawing to electron donating substitutions can be conveniently synthesized using the corresponding aryl boronic acid and N-acyloxyphthalimide.
- Gao, Feng,Feng, Huangdi,Sun, Zhihua
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p. 6451 - 6454
(2014/12/10)
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- FAMILY OF ARYL, HETEROARYL, O-ARYL AND O-HETEROARYL CARBASUGARS
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The present invention relates to a compound of the following formula (I): as well as its process of preparation, pharmaceutical and cosmetics composition comprising it and use thereof, notably as an inhibitor of the sodium-dependent glucose co-transporter, such as SGLTl, SGLT2 and SGLT3, in particular in the treatment or prevention of diabetes, and more particularly type-II diabetes, diabetes-related complications, such as arthritis of the lower extremities, cardiac infarction, renal insufficiency, neuropathy or blindness, hyperglycemia, hyperinsulinemia, obesity, hypertriglyceridemia, X syndrome and arteriosclerosis, as well as for its use as an anticancer, anti-infective, anti-viral, anti-thrombotic or anti- inflammatory drug, or for lightening, bleaching, depigmenting the skin, removing blemishes from the skin, particularly age spots and freckles, or preventing pigmentation of the skin.
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- A zeolite imidazolate framework ZIF-8 catalyst for Friedel-Crafts acylation
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A zeolite imidazolate framework, ZIF-8, was synthesized and characterized by dynamic laser light scattering, X-ray powder diffraction, scanning electron microscopy, transmission electron microscopy, thermogravimetric analysis, Fourier transform infrared, atomic absorption spectrophotometry, and nitrogen adsorption measurements. The ZIF-8 was highly crystalline and porous with a surface area of over 1600 m2/g. Friedel-Crafts acylation of anisole and benzoyl chloride proceeded well in the presence of ZIF-8 (2-6 mol%) without the need for an inert atmosphere. The reaction afforded a selectivity of 93%-95% to the p-isomer. The solid catalyst can be separated from the reaction mixture by simple centrifugation and reused without significant degradation in catalytic activity. There was no leaching of active acid species into the reaction solution.
- Nguyen, Lien T.L.,Le, Ky K.A.,Phan, Nam T.S.
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experimental part
p. 688 - 696
(2012/08/08)
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- Synthesis of diaryl ketones via a phosphine-free Fukuyama reaction
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The synthesis of unsymmetrical diaryl ketones via the Fukuyama coupling of thioesters and organozinc reagents is described. Typically, the synthesis of diaryl ketones using this methodology provides low yields. The simple complex, Pd(dba)2, was found to convert a variety of aryl thioesters to diaryl ketones in good yields. The Royal Society of Chemistry 2011.
- Kunchithapatham, Kamala,Eichman, Chad C.,Stambuli, James P.
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supporting information; experimental part
p. 12679 - 12681
(2012/01/05)
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- Photochemically promoted transition metal-free cross-coupling of acylsilanes with organoboronic esters
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Intermolecular carbon-carbon bond formation between acylsilanes and organoboronic esters was achieved by photoirradiation under almost neutral, transition metal-free conditions. In this reaction, siloxycarbenes generated by photoisomerization of acylsilanes reacted with boronic esters to give the formal B-C bond insertion intermediates, which underwent unique rearrangement to afford the cyclic α-alkoxyboronic esters. Acidic treatment of the resulting crude products under air furnished the cross-coupled ketones in good yields.
- Ito, Kazuta,Tamashima, Hiroto,Iwasawa, Nobuharu,Kusama, Hiroyuki
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scheme or table
p. 3716 - 3719
(2011/05/14)
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- Synthesis of arylketones by ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids
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The first ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids is reported. Various aliphatic and aromatic aldehydes are transformed to the corresponding arylketones. A total of 31 examples with moderate to excellent yields are presented, together with the results of an initial mechanistic investigation.
- Li, Hong,Xu, Yuan,Shi, Erbo,Wei, Wei,Suo, Xiangqiang,Wan, Xiaobing
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supporting information; experimental part
p. 7880 - 7882
(2011/08/06)
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- Aryl ketone synthesis via tandem orthoplatinated triarylphosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation
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Tandem orthoplatinated triaryl phosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation to yield aryl ketones is described. 3-Pentanone was identified as a suitable oxidant for the tandem aryl ketone formation reaction. By using microwave energy, aryl ketones were obtained in high yields with the catalyst loading as low as 0.01%.
- Liao, Yuan-Xi,Hu, Qiao-Sheng
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supporting information; experimental part
p. 6986 - 6989
(2010/11/17)
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- Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3
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Aromatic compounds react smoothly with carboxylic acids in the presence of silica gel supported aluminium trichloride to afford the corresponding ketones with high regioselectivity in high to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency. tuebitak.
- Parvanak Boroujeni, Kaveh
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experimental part
p. 621 - 630
(2010/11/04)
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- Sterically hindered benzophenones via rhodium-catalyzed oxidative arylation of aldehydes
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(Chemical Equation Presented) Efficient cross-coupling, allowing a straightforward access to congested benzophenones, between aromatic aldehydes and potassium aryltrifluoroborates, is described in the presence of a rhodium/tri-tert-butylphosphane catalyst system and acetone as cosolvent. The use of the stable phosphonium salts of tri-tert-butylphosphane prevented the use of highly oxidizable tri-tert-butylphosphane and allowed a careful control of the stoichiometry with the rhodium.
- Chuzel, Olivier,Roesch, Alexander,Genet, Jean-Pierre,Darses, Sylvain
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p. 7800 - 7802
(2008/12/22)
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- A general synthesis of diarylketones by means of a three-component cross-coupling of aryl and heteroaryl bromides, carbon monoxide, and boronic acids
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Pd(OAc)2/di-1-adamantyl-n-butylphosphine (cataCXium A) is highly active in the three-component Suzuki carbonylation and represents the most general catalyst system reported up to now. A broad range of aryl/heteroaryl bromides and aryl boronic acids can be coupled to the corresponding diarylketones at low catalyst loadings.
- Neumann, Helfried,Brennfuehrer, Anne,Beller, Matthias
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experimental part
p. 3645 - 3652
(2009/04/11)
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- Synthesis of sterically hindered ortho-substituted tetraphenylethenes. Electronic effects in the McMurry olefination reaction
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Contrary to literature consensus, the McMurry olefination reaction can be extended to the direct synthesis of sterically encumbered tetrakis(2- substituted) tetraphenylethenes from the corresponding 2,2′-disubstituted benzophenones. The reaction exploits
- Chung, Mee-Kyung,Qi, Guizhong,Stryker, Jeffrey M.
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p. 1491 - 1494
(2007/10/03)
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- Novel aromatic fluoroglycoside derivatives, medicaments containing these compounds, and the use thereof
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Novel aromatic fluoroglycoside derivatives, medicaments containing these compounds, and the use thereof. The invention relates to substituted aromatic fluoroglycoside derivatives of the formula I in which the radicals have the stated meanings, and their p
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Page/Page column 23
(2008/06/13)
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- Palladium-catalyzed carboacylation of alkenes by using acylchromates as acyl donors
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Palladium-catalyzed arylacylation of alkenes proceeds by employing acylchromates as acyl donors. When active alkenes such as norbornene and methoxyallene are treated with an aryl iodide, an acylchromate, and a catalytic amount of Pd(OAc)2/2P(o-Tol)3, arylacylation of these alkenes proceeds at room temperature. From aryl iodides having an intramolecular alkene moiety, cyclization-acylation products are obtained via intramolecular arylpalladation followed by acylation with acylchromates.
- Yamane, Motoki,Kubota, Yuko,Narasaka, Koichi
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p. 331 - 340
(2007/10/03)
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- A new catalytic oxidation of diarylmethanes mediated by 2,2',3,3',5,5'- hexaphenyl-(1,1'-biphenyl)-4,4'-dioxyl
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Diarylmethanes were catalytically oxidized with oxygen to benzophenones with a Cu(I)CI catalyst in butyronitrile as solvent in the presence of the mediating agent 2,2',3,3',5,5'-hexaphenyl-(1,1'-biphenyl)-4,4'-dioxyl 1, which was generated in situ from 2,2',3,3',5,5'-hexaphenyl-(1,1'-biphenyl)- 4-4'-diol 4.
- Barbiero,Kim,Hay
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p. 5833 - 5836
(2007/10/02)
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- The catalytic Friedel-Crafts acylation reaction starting from aromatic compounds and free carboxylic acids (or their trimethylsilyl esters) by promotion of silicon (IV) cationic species via mixed anhydrides
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In the presence of active cationic species generated from silicon(IV) chloride and silver perchlorate, carboxylic acids or their trimethylsilyl esters react with p-trifluoromethylbenzoic anhydride to form corresponding mixed anhydrides in situ. Then the catalytic Friedel-Crafts acylation reaction between initially formed mixed anhydrides and coexisted aromatic compounds smoothly proceeds at room temperature to afford the corresponding aromatic ketones in high yields. The above two sequential reactions are effectively promoted by the active silicon(IV) catalyst under mild conditions.
- Suzuki,Kitagawa,Mukaiyama
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p. 3729 - 3734
(2007/10/02)
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- SOME RELATIONSHIPS GOVERNING THE DEACYLATION OF SUBSTITUTED 9-BENZOYLANTHRACENES
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In the presence of small amounts of ferric chloride substituted 9-benzoylanthracenes are deacylated, isomerized, and reacylated.The degree of transformation of the ketones increases with increase in the effective volume of the substituent at the ortho position to the acyl and with increase in the electron-donating characteristics of the substituent in the aromatic rings.
- Bokova, A. I.,Buchina, I. K.
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p. 1199 - 1201
(2007/10/02)
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- Carboxylic Trifluoromethanesulfonic Anhydrides as Highly Effective Acylation Agents. - Perfluoroalkanesulfonic Acid Catalyzed Acylation of Arenes
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Arene- and alkanecarboxylic trifluoromethanesulfonic anhydrides 2 and 5 are highly effective acylation agents, which react without Friedel-Crafts catalysts even with deactivated aromatics to yield aryl ketones 3 and 6, respectively.Acylation of arenes with carbonyl chlorides 4 and catalytic amounts of perfluoroalkanesulfonic acid gives ketones 3 and 6, resp., in good yields.Under similar conditions other strong Broensted acids show a considerably smaller degree of catalytic effect.
- Effenberger, Franz,Sohn, Erich,Epple, Gerhard
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p. 1195 - 1208
(2007/10/02)
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- Benzophenones and benzhydrols
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Compounds having the formula STR1 WHERE X is --CO-- or --CHOH--, Y and Z are halogen, alkyl, trifluoromethyl, alkoxy, hydroxy, nitro, cyano, carboxy, carbalkoxy, carbamoyl, or alkylthio, and m and n are 0, 1, or 2 Are useful in controlling undesirable secondary growth in plants, particularly sucker growth in tobacco.
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