75731-44-1Relevant articles and documents
Palladium-catalyzed cross-coupling of aroyl chlorides with aryl stannanes in the presence of triethylsilane: Efficient access to aromatic ketones
Higashi, Shoko,Uno, Sota,Ohsuga, Yui,Noumi, Maiko,Saito, Ryota
supporting information, (2020/10/12)
Herein, we report the development of a palladium-catalyzed cross-coupling reaction that focuses on the preparation of aromatic ketones. Aroyl chlorides react quickly at 120 °C with aryl stannanes in the presence of Pd(PPh3)4 and Et3SiH to efficiently give the corresponding ketones without the formation of significant decarbonylated byproducts. In other words, the decarbonylative side reaction is practically suppressed by simply adding Et3SiH to the reaction mixture, which reduces the amount of biaryl impurities in the products.
N-Acylsuccinimides: Efficient acylative coupling reagents in palladium-catalyzed Suzuki coupling via C–N cleavage
Cui, Ming,Chen, Zeyu,Liu, Tingting,Wang, Hui,Zeng, Zhuo
, p. 3819 - 3822 (2017/09/15)
An acylative Suzuki coupling of activated amides with aryl boronic acids has been reported via palladium-catalyzed C–N bond cleavage. This protocol demonstrate amides can be activated by an atom-economic and cheap succinimide, which can be efficiently utilized to synthesize broad array of diaryl ketones in moderate to good yields.
Iron-catalyzed carbonylation of aryl halides with arylborons using stoichiometric chloroform as the carbon monoxide source
Zhao, Hongyuan,Du, Hongyan,Yuan, Xiaorong,Wang, Tianjiao,Han, Wei
supporting information, p. 5782 - 5787 (2016/11/06)
A general iron-catalyzed carbonylative Suzuki-Miyaura coupling of aryl halides with arylborons is reported, using stoichiometric CHCl3 as the CO source. The high efficiency, economy, selectivity, and operational simplicity of this transformation make this method a valuable tool in organic synthesis. Importantly, the presented strategy allows effective 13C labeling simply by using the commercially available 13C-labeled CHCl3. On the basis of the initial mechanistic exploration, an aryl radical intermediate is proposed in the present carbonylation process.
Palladium-catalyzed Suzuki-Miyaura coupling of amides by carbon-nitrogen cleavage: General strategy for amide N-C bond activation
Meng, Guangrong,Szostak, Michal
supporting information, p. 5690 - 5707 (2016/07/06)
The first palladium-catalyzed Suzuki-Miyaura cross-coupling of amides with boronic acids for the synthesis of ketones by sterically-controlled N-C bond activation is reported. The transformation is characterized by operational simplicity using bench-stable, commercial reagents and catalysts, and a broad substrate scope, including substrates with electron-donating and withdrawing groups on both coupling partners, steric-hindrance, heterocycles, halides, esters and ketones. The scope and limitations are presented in the synthesis of >60 functionalized ketones. Mechanistic studies provide insight into the catalytic cycle of the cross-coupling, including the first experimental evidence for Pd insertion into the amide N-C bond. The synthetic utility is showcased by a gram-scale cross-coupling and cross-coupling at room temperature. Most importantly, this process provides a blueprint for the development of a plethora of metal catalyzed reactions of typically inert amide bonds via acyl-metal intermediates. A unified strategy for amide bond activation to enable metal insertion into N-C amide bond is outlined (Scheme 1).
Synthesis of ketones via organolithium addition to acid chlorides using continuous flow chemistry
Moon, Soo-Yeon,Jung, Seo-Hee,Bin Kim,Kim, Won-Suk
, p. 79385 - 79390 (2015/10/06)
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.
Palladium-catalyzed cross-coupling of 2-aryl-1,3-dithianes
Dockrey, Summer A. Baker,Makepeace, Alicia K.,Schmink, Jason R.
, p. 4730 - 4733 (2015/04/27)
Palladium-catalyzed cross-coupling of aryl bromides with 2-aryl-1,3-dithianes is described. This methodology takes advantage of the relatively acidic benzylic proton of the dithiane, allowing it to act as a competent, polarity-reversed transmetalation reagent. This unique approach affords the ability to employ an orthogonal deprotection strategy, and practical routes to both diaryl ketones and diarylmethanes are illustrated. Cross-coupling of a range of aryl dithianes with aryl bromides, including scope and current limitations, is presented.
Nickel-catalyzed cross-coupling of carboxylic anhydrides with arylboronic acids
Chen, Qiang,Fan, Xin-Heng,Zhang, Li-Peng,Yang, Lian-Ming
, p. 53885 - 53890 (2015/01/16)
A nickel-based catalyst was employed in the cross-coupling of carboxylic anhydrides with arylboronic acids, and the reaction was carried out under mild conditions. This new protocol provides an efficient, cheap and convenient alternative to synthesizing aromatic ketones.
Chloro-ruthenium complexes with carbonyl and N-(aryl)pyridine-2-aldimines as ancillary ligands. Synthesis, characterization and catalytic application in C-C cross-coupling of arylaldehydes with arylboronic acids
Dey, Bikash Kali,Dutta, Jayita,Drew, Michael G.B.,Bhattacharya, Samaresh
, p. 176 - 184 (2014/01/06)
Reaction of N-(aryl)pyridine-2-aldimines (L-R, R = OCH3, CH 3, H, Cl and NO2) with [Ru(CO)2Cl 2]n in refluxing ethanol affords a group of complexes of type [Ru(L-R)(CO)2Cl2]. In these complexes the diimine ligands (L-R) are coordinated to the metal center as NN-donors forming five-membered chelate rings, the carbonyls are mutually cis and the two chlorides are trans. Crystal structure of [Ru(L-OCH3)(CO) 2Cl2] has been determined. All the complexes show characteristic 1H NMR signals, and in dichloromethane solution they display intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows an irreversible oxidation of the metal center within 1.15-1.23 V vs SCE, and reduction(s) of the diimine ligand within -0.70 to -0.96 V vs SCE. The [Ru(L-R)(CO)2Cl2] complexes efficiently catalyze cross-coupling of arylaldehydes with arylboronic acids yielding diaryl ketones.
Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
Luong, Martín,Domini, Claudia E.,Silbestri, Gustavo F.,Chopa, Alicia B.
, p. 43 - 48 (2013/02/21)
A series of diaryl ketones have been synthesized in moderate to excellent yields through the selective cross-coupling reaction of benzoyl chlorides with arylstannanes using a sonochemical variation of the Stille coupling. Ultrasound significantly enhances this useful organometallic transformation affording the desired products in higher yields and shorter reaction times than conventional reactions. The scope of the protocol has been explored with a selection of arylstannanes and different aroyl chlorides as reaction partners. Remarkably, no by-products resulting from homo-coupling could be detected. The ultrasound-promoted cross-coupling reaction was optimized through experimental design.
Novel organosoluble polyimide based on an asymmetric bis(ether amine): 3, 4′-Bis(4-aminophenoxy)-benzophenone
Bu, Qian Qian,Zhang, Shu Jiang,Li, Hui,Li, Yan Feng
experimental part, p. 121 - 122 (2012/03/27)
A new kind of asymmetrical ether diamine, 3,4′-bis(4-aminophenoxy) benzophenone (BABP), was synthesized from the nucleophilic substitution reaction of 4-chloronitrobenzene and 3,4′-dihydroxybenzophenone in the presence of potassium carbonate, followed by catalytic reduction with SnCl 2·6H2O and concentrated hydrochloric acid. The prepared diamine was employed in the preparation of a novel polyimide containing asymmetrical diaryl ether segments via the polycondensation of it with BTDA by a two-step method. The resulting polyimide exhibits excellent solubility, film-forming capability and high thermal resistance.
