34328-31-9Relevant academic research and scientific papers
Binuclear Palladium Complex Immobilized on Mesoporous SBA-16: Efficient Heterogeneous Catalyst for the Carbonylative Suzuki Coupling Reaction of Aryl Iodides and Arylboronic Acids Using Cr(CO)6 as Carbonyl Source
Niakan, Mahsa,Asadi, Zahra,Emami, Mohammad
, p. 404 - 418 (2020/01/03)
Abstract: In this study, a binuclear palladium complex immobilized on the organo-functionalized SBA-16 was prepared and structurally characterized by routine techniques. Characterizations indicated that the mesostructure of SBA-16 was maintained after the immobilization of palladium complex. Then, the prepared nanomaterial was applied as a heterogeneous catalyst in the carbonylative Suzuki coupling reaction of aryl iodides with arylboronic acids using Cr(CO)6 as carbonyl source. The catalyst was efficiently promoted the coupling reactions of various aryl iodides and arylboronic acids to give the corresponding diaryl ketones in excellent yields. Moreover, the catalyst was readily recovered by filtration and could be reused for seven cycles without losing its structural integrity and catalytic activity. Graphic Abstract: [Figure not available: see fulltext.].
I-Pr2NMgCl·LiCl Enables the Synthesis of Ketones by Direct Addition of Grignard Reagents to Carboxylate Anions
Colas, Kilian,Dos Santos, A. Catarina V. D.,Mendoza, Abraham
supporting information, (2019/10/08)
The direct preparation of ketones from carboxylate anions is greatly limited by the required use of organolithium reagents or activated acyl sources that need to be independently prepared. Herein, a specific magnesium amide additive is used to activate and control the addition of more tolerant Grignard reagents to carboxylate anions. This strategy enables the modular synthesis of ketones from CO2 and the preparation of isotopically labeled pharmaceutical building blocks in a single operation.
Photo-nickel dual catalytic benzoylation of aryl bromides
Schirmer, Tobias Emanuel,Wimmer, Alexander,Weinzierl, Florian Wolfgang Clemens,K?nig, Burkhard
supporting information, p. 10796 - 10799 (2019/09/13)
The dual catalytic arylation of aromatic aldehydes by aryl bromides using UV-irradiation and a nickel catalyst is reported. The reaction product serves as a photocatalyst and a hydrogen atom transfer agent for this transformation.
Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C–CN Bond Activation
Liu, Kui,Tao, Shou-Wei,Qian, Chun,Zhu, Yong-Ming
supporting information, p. 4769 - 4775 (2018/09/06)
A Pd-catalyzed Suzuki–Miyaura cross-coupling reaction between arylboronic acids and α-iminonitriles has been developed. The reaction proceeds through selective activation of the C–CN bond, tolerates a wide range of substituents, and delivers the versatile ketone products in moderate to excellent yields.
Base free Suzuki acylation reactions of sodium (aryl trihydroxyborate) salts: A novel synthesis of substituted aryl ketones
Sithebe, Siphamandla,Molefe, Patience
, p. 305 - 311 (2017/07/13)
The first simple and efficient base free Pd(PPh3)4 catalysed synthesis of substituted aryl ketones from acyl chlorides and easily accessible sodium aryl trihydroxyborate salts in aqueous toluene is reported. The reaction conditions appeared versatile and tolerable to a variety of functional groups including, CF3, OMe, SMe, Br, NO2, F, OH and NH2 furnishing 25 examples of substituted aryl ketones in isolated yields of up to 96% in 24 h. Beside the high purity, the ease and convenience of the isolation compared to boronic acids, sodium aryl trihydroxyborate salts could be used subsequently without the addition of excess amount of an activator and are more user-friendly in terms of the use of accurate reaction stoichiometry.
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.
Analogues of fenarimol are potent inhibitors of trypanosoma cruzi and are efficacious in a murine model of chagas disease
Keenan, Martine,Abbott, Michael J.,Alexander, Paul W.,Armstrong, Tanya,Best, Wayne M.,Berven, Bradley,Botero, Adriana,Chaplin, Jason H.,Charman, Susan A.,Chatelain, Eric,Von Geldern, Thomas W.,Kerfoot, Maria,Khong, Andrea,Nguyen, Tien,McManus, Joshua D.,Morizzi, Julia,Ryan, Eileen,Scandale, Ivan,Thompson, R. Andrew,Wang, Sen Z.,White, Karen L.
supporting information; experimental part, p. 4189 - 4204 (2012/07/27)
We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC50s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.
Ionically tagged benzimidazole palladium(II) complex: Preparation and catalytic application in cross-coupling reactions
Zhang, Li,Wu, Junliang,Shi, Lijun,Xia, Chungu,Li, Fuwei
supporting information; experimental part, p. 3897 - 3901 (2011/08/09)
An imidazolium chloride tagged palladium(II) complex has been conveniently prepared and structurally analyzed. It is active toward cross-coupling of arylboronic acid with aryl halide and benzoyl chloride, giving moderate to high yield of the desired biaryls and aryl ketones, respectively. The present phosphine-free (N-N)Pd(II) complex could be efficiently recycled at least four times with minor decrease of activity in the aqueous Suzuki-Miyaura coupling reaction.
Synthesis of aryl ketones by cross-coupling reaction of arylboronic acids with carboxylic anhydrides in aqueous phase
Xin, Bing-Wei
experimental part, p. 2826 - 2837 (2009/04/04)
A highly efficient aqueous system of PdCl2-catalyzed cross-coupling reaction of arylboronic acid with carboxylic anhydride (Suzuki-type reaction) without the use of phosphine ligands was developed. The reactions went smoothly in acetone/H2O phase to give good yields of aryl ketones in short reaction times (1-3 h) at room temperature in air and were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic anhydrides. Copyright Taylor & Francis Group, LLC.
The surfactant-promoted cross-coupling reactions of arylboronic acids with carboxylic anhydrides or acyl chlorides in water
Xin, Bingwei,Zhang, Yuhong,Cheng, Kai
, p. 1970 - 1978 (2008/02/12)
The palladium(II) chloride catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides in water in the presence of various surfactants is described. The inexpensive and industrially widely used sodium dodecyl sulfate (SDS) was found to be a good promoter of the coupling reaction and aryl ketones were obtained in good yields without the use of phosphine ligands. The reactions were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic derivatives and a variety of aryl ketones were obtained under mild conditions in air. Georg Thieme Verlag Stuttgart.
