- N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
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We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.
- Ishii, Takuya,Kakeno, Yuki,Nagao, Kazunori,Ohmiya, Hirohisa
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supporting information
p. 3854 - 3858
(2019/04/25)
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- Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups
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A novel protocol for ortho-C-H alkylation of aromatic and heteroaromatic ketones and esters under Cp?Co(III) catalysis has been developed for the first time. The reaction proceeds through initial cyclometalation via weak chelation-assisted C-H bond activation, followed by coordination of activated alkene, insertion between Co-C, and protodemetalation.
- Mandal, Rajib,Emayavaramban, Balakumar,Sundararaju, Basker
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supporting information
p. 2835 - 2838
(2018/05/29)
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- AMIDE COMPOUNDS AS TRYPTOPHAN HYDROXYLASE INHIBITORS
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The present invention is directed to amide compounds which are inhibitors of tryptophan hydroxylase (TPH), particularly isoform 1 (TPH1), that are useful in the treatment or prevention of diseases or disorders associated with peripheral serotonin including, for example, gastrointestinal, cardiovascular, pulmonary, inflammatory, metabolic, fibrotic, and low bone mass diseases, as well as cancer.
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Page/Page column 70-71
(2016/07/27)
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- Synthesis and methemoglobinemia-inducing properties of analogues of para-aminopropiophenone designed as humane rodenticides
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A number of structural analogues of the known toxicant para- aminopropiophenone (PAPP) have been prepared and evaluated for their capacity to induce methemoglobinemia - with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed for alkyl analogues of PAPP (aminophenones 1-20; compound 6 metHb% = 74.1 ± 2). Besides lipophilicity, this structural sub-class suggested there were certain structural requirements for activity, with both branched (10-16) and cyclic (17-20) alkyl analogues exhibiting inferior in vitro metHb induction. Of the four candidates (compounds 4, 6, 13 and 23) evaluated in vivo, 4 exhibited the greatest toxicity. In parallel, aminophenone bioisosteres, including oximes 30-32, sulfoxide 33, sulfone 34 and sulfonamides 35-36, were found to be inferior metHb inducers to lead ketone 4. Closer examination of Hammett substituent constants suggests that a particular combination of the field and resonance parameters may be significant with respect to the redox mechanisms behind PAPPs metHb toxicity.
- Rennison, David,Conole, Daniel,Tingle, Malcolm D.,Yang, Junpeng,Eason, Charles T.,Brimble, Margaret A.
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supporting information
p. 6629 - 6635
(2014/01/06)
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- Ultrasound assisted Friedel-Crafts acylation of aromatics using ferric sulphate as catalyst
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The use of ultrasound in the acylation reactions of various aromatics and polyaromatics with different acyl chlorides, in the presence of catalytic amount of ferric sulphate at room temperature, gives good yields of the respective ketones with a short reaction time. A facile and simple synthesis of various aromatic ketones using Friedel-Crafts acylation has been established from the corresponding acid chlorides and aromatic or polyaromatic compounds, respectively under mild reaction conditions with shorter reaction times (30-45 min) and in reasonable yields. This method offers the advantage of low cost and ease of purification of the products because of the small amount of ferric sulphate used in these reactions.
- Sridharan, Anandhi,Gopalakrishnan, Geetha
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experimental part
p. 1192 - 1195
(2011/10/18)
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- Copper-catalyzed hydrosilylation with a bowl-shaped phosphane ligand: Preferential reduction of a bulky ketone in the presence of an aldehyde
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Chemical Equation Presented Hollywood bowl: A highly active copper catalyst with a bowl-shaped phosphane (bsp) ligand was used in the hydrosilylation reaction of bulky ketones. The preferential reduction of a bulky ketone in the presence of an unprotected aldehyde is unprecedented.
- Fujihara, Tetsuaki,Semba, Kazuhiko,Terao, Jun,Tsuji, Yasushi
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supporting information; experimental part
p. 1472 - 1476
(2010/05/02)
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- Facile synthesis of pivalophenones by an ultrasound assisted iodine catalysed Friedel-Crafts acylation reaction
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The use of ultrasound in the acylation reactions of various aromatics and heterocyclics with pivaloyl chloride in the presence of catalytic amount of iodine, without any added solvent and at room temperature, gives excellent yields of the respective pivalophenones in a short reaction time.
- Gopalakrishnan, Geetha,Anandhi,Narasimhan
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p. 1197 - 1198
(2007/10/03)
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- A facile synthesis of pivalophenones by ultrasound assisted AlCl3 catalysed Friedel-Crafts reaction
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Pivalophenones have been prepared by the acylation reaction of various aromatic and heterocyclic compounds with pivaloyl chloride using AlCl3 as catalyst under sonochemical conditions in a short reaction time and in reasonable yields.
- Gopalakrishnan, Geetha,Anandhi,Narasimhan
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p. 1194 - 1196
(2007/10/03)
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- A Convenient Procedure for Complete Methylation of the α-Positions of Some Ketones
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2,2,6,6-Tetramethylcyclohexanone (2a), Pivalophenone (4a), and other complete methylated ketones can be prepared by a simple procedure.Therefore the ketone was treated with methyl iodide and powdered KOH in the presence of catalytical amounts of crown-6.
- Lissel, Manfred,Neumann, Beate,Schmidt, Stefan
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p. 263 - 264
(2007/10/02)
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