51770-83-3Relevant academic research and scientific papers
Polymer-Anchored Bifunctional Pincer Catalysts for Chemoselective Transfer Hydrogenation and Related Reactions
Mujahed, Shrouq,Valentini, Federica,Cohen, Shirel,Vaccaro, Luigi,Gelman, Dmitri
, p. 4693 - 4699 (2019/10/28)
A series of polymer-supported cooperative PC(sp3)P pincer catalysts was synthesized and characterized. Their catalytic activity in the acceptorless dehydrogenative coupling of alcohols and the transfer hydrogenation of aldehydes with formic acid as a hydrogen source was investigated. This comparative study, examining homogeneous and polymer-tethered species, proved that carefully designing a link between the support and the catalytic moiety, which takes into consideration the mechanism underlying the target transformation, might lead to superior heterogeneous catalysis.
Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
, p. 11823 - 11838 (2019/10/02)
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.
Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids
Roslin, Sara,Odell, Luke R.
supporting information, p. 6895 - 6898 (2017/07/10)
Herein, a simple and efficient method for the palladium-catalyzed carbonylation of aryl boronic acids with unactivated alkyl iodides and bromides under visible-light irradiation, ambient temperature and low CO-pressure is presented. Notably, the procedure uses readily available equipment and an inexpensive palladium catalyst to generate the key alkyl radical intermediate. These mild conditions enabled the synthesis of a range of functionalized aryl alkyl ketones including the antipsychotic drug, melperone.
Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents
Dohi, Souya,Moriyama, Katsuhiko,Togo, Hideo
experimental part, p. 6557 - 6564 (2012/08/27)
Various diaryl ketones, alkyl aryl ketones, and dialkyl ketones were efficiently prepared in good yields by the reactions of the Grignard reagents derived from aryl or alkyl bromides, followed by the reactions with aromatic or aliphatic aldehydes and the subsequent treatment with 1,3-diiodo-5,5- dimethylhydantoin and K2CO3, in a one-pot method. The same treatment of aromatic bromides bearing electron-withdrawing groups, such as ester, nitrile, ketone, and nitro groups with i-PrMgCl·LiCl or PhMgCl instead of Mg, also provided the corresponding diaryl and alkyl aryl ketones in good yields. The above methods are simple and practical transition-metal-free methods for the preparation of various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatic groups and electron-deficient aromatic groups, as well as dialkyl ketones.
Friedel-crafts acylation of arenes with carboxylic acids using polystyrene-supported aluminum triflate
Boroujeni, Kaveh Parvanak,Parvanak, Kamran
experimental part, p. 155 - 163 (2012/01/02)
Cross-linked polystyrene-supported aluminum triflate (Ps-Al(OTf) 3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for the acylation of aromatic compounds. The catalyst can be easily prepared from cheap starting materials, is stable (as a bench top catalyst) and is reusable.
Direct synthesis of aryl ketones by palladium-catalyzed desulfinative addition of sodium sulfinates to nitriles
Liu, Jing,Zhou, Xianya,Rao, Honghua,Xiao, Fuhong,Li, Chao-Jun,Deng, Guo-Jun
supporting information; experimental part, p. 7996 - 7999 (2011/08/22)
Mild yet direct: A convenient and efficient method for the synthesis of various aryl ketones by palladium-catalyzed desulfinative addition of aromatic sulfinic acid sodium salts to various nitriles is described (see scheme). Aromatic and aliphatic nitriles are successfully reacted with arenesulfinic acid sodium salts to form aryl ketones in good yields.
Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3
Parvanak Boroujeni, Kaveh
experimental part, p. 621 - 630 (2010/11/04)
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.
Block of human NaV 1.5 sodium channels by novel α-hydroxyphenylamide analogues of phenytoin
Lenkowski, Paul W.,Ko, Seong-Hoon,Anderson, James D.,Brown, Milton L.,Patel, Manoj K.
, p. 635 - 644 (2007/10/03)
Voltage-gated sodium (Na) channels are a critical component of electrically excitable cells. Phenytoin (diphenylhydantoin, DPH) is an established sodium channel blocker and is a useful anticonvulsant and class 1b antiarrhythmic, and has been effectively used in the treatment of neuropathic pain. In this study, we have synthesized novel α-hydroxyphenylamide analogues of diphenylhydantoin and examined their ability to inhibit human Nav1.5 sodium channels expressed in Chinese Hamster Ovary (CHO-K1) cells. Phenyl ring substitutions were examined including para-methyl, para-fluoro, para-chloro, ortho-chloro and meta-chloro. We have found that phenyl ring substitutions with electron withdrawing properties resulted in compounds with greater activity. In comparison to diphenylhydantoin, the novel chloro-substituted α-hydroxyphenylamide compounds produced as much as a 20-fold greater tonic and frequency-dependent blockade of Nav1.5 channels with an IC50 value of 14.5μM. In addition, the chloro-substitutions have position specific state dependent blocking properties. The ortho-, meta- and para-chloro substitutions have an 8-, 13- and 3-fold increased affinity for the inactivated state, respectively. Molecular modeling suggests that these differences in affinity are due to a direct interaction with the receptor. Comparing models of diphenylhydantoin to the novel α-hydroxyphenlyamide compound suggests that the increased activity may be due to an optimized phenyl ring position and increased molecular volume. This information may be useful in the development of more potent sodium channel blockers.
Efficient acylation of toluene and anisole with aliphatic carboxylic acids catalysed by heteropoly salt Cs2.5H0.5PW12O40
Kaur, Jaspal,Kozhevnikov, Ivan V.
, p. 2508 - 2509 (2007/10/03)
Heteropoly salt Cs2.5H0.5PW12O40 is a highly efficient and reusable solid acid catalyst for the liquid-phase acylation of toluene or anisole with C2 - C12 aliphatic carboxylic acids.
SYNTHESE ET ETUDE DE LA DEGRADATION PHOTOCHIMIQUE DE TENSIO-ACTIFS CATIONIQUES PHOTOCLIVABLES
Strub-Leconte, M. P.,Riess, G.
, p. 137 - 144 (2007/10/02)
A homologous series of photocleavable cationic surfactants was prepared.These aryl-alkyl-ketone type surfactants have the following structure .Their critical micelle concentration in water was determined.The photodegradation study has shown that the cleavage occurs with a high quantum yield by a Norrish II mechanism with formation of alkene, substituted acetophenone and cyclobutanols.The photochemical yield of cleavage reaches 75 percent with formation of a hydrophilic (substituted acetophenone) and a hydrophobic derivative (alkene).
