- Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
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Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
- Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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p. 11823 - 11838
(2019/10/02)
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- Acyl hydrazides as acyl donors for the synthesis of diaryl and aryl alkyl ketones
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In this communication we describe a novel strategy for the formation of valuable diaryl and aryl alkyl ketones from acyl hydrazides. A wide variety of ketones are prepared and the mild reaction conditions allow for the use of a range of functionalities, especially in the synthesis of diaryl ketones.
- Akhbar, Ahmed R.,Chudasama, Vijay,Fitzmaurice, Richard J.,Powell, Lyn,Caddick, Stephen
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p. 743 - 746
(2014/01/06)
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- Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis
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The enantioselective α-arylation of aldehydes has been accomplished using diaryliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable α-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.
- Allen, Anna E.,MacMillan, David W. C.
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supporting information; experimental part
p. 4260 - 4263
(2011/06/21)
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- Designed synthesis of multi-electrochromic systems bearing diaryl ketone and isophthalates
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New multi-electrochromic systems have been developed through the combination of a diaryl ketyl radical system with isophthalate-based electrochromic materials. The location of the isophthalate group in compounds is very critical to obtaining different colors in the multi-electrochromism.
- Sharmoukh,Ko, Kyoung Chul,Noh, Changho,Lee, Jin Yong,Son, Seung Uk
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supporting information; experimental part
p. 6708 - 6711
(2010/12/19)
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- A one-pot method for the iodination of aryl amines via stable aryl diazonium silica sulfates under solvent-free conditions
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A convenient and rapid one-pot method for the synthesis of iodoarenes is developed which involves the sequential diazotization-iodination of aromatic amines with sodium nitrite, silica sulfuric acid and potassium iodide under solvent-free conditions at room temperature. Various aromatic amines possessing electron-withdrawing groups or electron-donating groups are converted into the corresponding aryl iodides in good yields. Georg Thieme Verlag Stuttgart.
- Zarei, Amin,Hajipour, Abdol R.,Khazdoozd, Leila
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experimental part
p. 941 - 944
(2009/12/02)
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- Synthesis and characterization of fullerene derivatives with perfluoroalkyl groups
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Two novel C60 fullerene derivatives containing one or two perfluorooctyl groups were designed and efficiently synthesized. Organic field-effect transistors based on the bisperfluorooctyl compound 1 show high mobility up to 6.7 × 10-2 cm2 V-1 s and high on/off ratio up to 5 × 107, which qualifies compound 1 as promising n-type conductor material. The Royal Society of Chemistry 2009.
- Wang, Xuemei,Guo, Yunlong,Xiao, Yi,Zhang, Lei,Yu, Gui,Liu, Yunqi
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supporting information; experimental part
p. 3258 - 3262
(2010/05/02)
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- A catalyst-free synthesis of asymmetric diaryl ketones from aryltins
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A series of diaryl ketones have been synthesized in good yields (40-78%) through the catalyst-free reaction of trimethylarylstannanes with aroyl chlorides in chlorobenzene as solvent. In addition, an attractive feature is that these reactions are completely regioselective making possible the synthesis of diarylketones which are not usually available under the influence of the directing forces of the substituents present in the aromatic ring. Also, the reaction conditions are mild enough to be applied to acid sensitive molecules.
- Silbestri, Gustavo F.,Masson, Romina Bogel,Lockhart, María T.,Chopa, Alicia B.
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p. 1520 - 1524
(2007/10/03)
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- Tetramethylammonium dichloroiodate: An efficient and environmentally friendly iodination reagent for iodination of aromatic compounds under mild and solvent-free conditions
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Tetramethylammonium dichloroiodate (1, TMADCI) as a mild and efficient iodination reagent was prepared. Iodination of different aromatic compounds with this reagent takes place fast and with high yields under solvent-free conditions.
- Hajipour, Abdol R.,Arbabian, Marty,Ruoho, Arnold E.
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p. 8622 - 8624
(2007/10/03)
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- Photoinduced Radical Cleavage of Iodobenzophenones
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The triplet state cleavage of m-iodo-(mibp) and p-iodobenzophenone (pIBP) to benzoylphenyl and iodine radicals has been studied by both steady state and laser flash techniques.Phosphorescence spectra in methanol/ ethanol glasses at 77 K indicate triplet energies of 68.4 and 67.8 kcal/mol for mIBP and pIBP, respectively.In most organic solvents products are benzophenone and iodinated solvents; these are formed by hydrogen abstraction from solvent by the initially formed benzoylphenyl radicals.Quantum yields for product formation decrease with increasing solvent viscosity, ranging from 0.45 in acetonitrile to 0.28 in cyclopentane and 0.05 in cyclooctane; they appear to reflect significant in-cage recoupling of the initial radical pairs.Quenching of the reaction by naphthalene indicates 25 degC triplet lifetimes of 25 and 0.2 ns for mIBP and pIBP, respectively, which were confirmed by flash kinetics.Laser excitation produced transient signals assigned to the iodine atom-toluene complex (in toluene) and, for mIBP, the triplet ketone.Decay of the latter revealed activation parameters ΔH = 4.0 +/- 0.2 kcal/mol and log A = 10.6 +/- 0.2 for mIBP in both methanol and toluene.The strong phosphorescence of both ketones at 77 K indicates that ΔH for pIBP must be >= 3kcal/mol, such that log A is ca. 12, much higher than for mIBP.The different rates and A values reflect different ?* spin densities at the meta and para positions in the lowest n,?* triplets, which react either by mixing with dissociative ?,?* states or by thermally converting into a dissociative ?,?* or ?1,?* state.The dependence of ?* spin density and the low A values strongly suggest an inefficient state interconversion at a surface crossing between n,?* and ?,?* states, because of their different symmetries.It is suggested that the low A values, which might indicate negative Δs values, are better understood as low transmission coefficients.
- Wagner, Peter J.,Waite, Carol I.
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p. 7388 - 7394
(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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