Article
Biochemistry & Molecular Biology
Laszlo Kollar, Adam Erdelyi, Haroon Rasheed, Attila Takacs
Summary: The study presents a novel synthetic method for producing N-acylnortropane derivatives of biological importance by aminocarbonylation reactions using tropane-based amines as N-nucleophiles and Pd(OAc)(2)/2 PPh3 catalysts, with the bidentate Xantphos ligand required for specific compounds. The resulting carboxamides were isolated and fully characterized, demonstrating the potential of this approach for accessing diverse structures of biologically relevant compounds.
Article
Chemistry, Organic
Sami Chniti, Laszlo Kollar, Attila Benyei, Agnes Dornyei, Attila Takacs
Summary: Novel N-substituted pyrrolo[3,4-b]quinoline-1,3-diones have been synthesized successfully through a highly selective palladium-catalyzed carbonylative imidazation-cyclization reaction. This method, applied for the first time to access original scaffolds, involves 3-bromo-2-iodoquinoline as a typical partner, primary amines, and atmospheric or high carbon monoxide pressure. The use of bidentate ligands such as XantPhos and dppp in atmospheric or high-pressure conditions provides a wide range of carbonylated compounds with good to excellent yields (up to 82%). Furthermore, new quinoline-2,3-dicarboxamides have been isolated as side products in very low yields and have been fully characterized. The solid state structures of three synthesized acridinimides have been unequivocally established by single-crystal XRD analysis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Sami Chniti, Laszlo Kollar, Attila Benyei, Attila Takacs
Summary: This research investigates the aminocarbonylation reaction of 6-iodoquinoline, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. The study shows that reaction conditions significantly influence the formation of amides and ketoamides, and by optimizing the conditions, selective synthesis of the desired products can be achieved.
Article
Chemistry, Multidisciplinary
Di Zhang, Youyuan Xiong, Yingjie Guo, Lei Zhang, Zheng Wang, Kuiling Ding
Summary: In this study, a Pd-catalyzed enantioselective domino Heck carbonylation reaction was developed using o-iodoacrylanilides, terminal alkynes, and water as nucleophiles. The reaction afforded a diverse range of beta-carbonylated 2-oxindole derivatives with a 3,3-disubstituted all-carbon quaternary stereocenter in high yields and good to excellent enantioselectivities. The synthetic utility of the methodology was demonstrated through gram-scale synthesis of various compounds, showcasing its potential for efficient chiral 2-oxindole synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Wenjun Luo, Fang Xu, Zhenguo Wang, Jiyan Pang, Zixu Wang, Zhixiu Sun, Aiyun Peng, Xiaohui Cao, Le Li
Summary: Unprecedented Staudinger reaction modes of secondary phosphine oxides (SPO) and organic azides are disclosed in this paper. Selective nitrogen atom exclusion from the azide group has been achieved by the use of various additives. Chlorotrimethylsilane mediates a stereoretentive Staudinger reaction with a 2-N exclusion, providing a valuable method for the synthesis of phosphinic amides, which can be considered complementary to the stereoinvertive Atherton-Todd reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A straightforward and selective method using carbon monoxide as a reductant was developed to prepare amides directly from nitroarenes and carboxylic acids. This protocol simplifies product isolation by not requiring any non-gaseous additives and preserves reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A simple and selective method using carbon monoxide as a reducing agent was developed for the preparation of amides from nitroarenes and carboxylic acids. The protocol does not require non-gaseous additives, simplifying product isolation and saving reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ning Liu, Xianqing Wu, Jingping Qu, Yifeng Chen
Summary: A nickel-catalyzed aminocarbonylation reaction of aromatic iodides with (hetero)aryl anilines and alkyl amines under atmospheric CO pressure is reported. This reaction exhibits a broad substrate scope and excellent functional group tolerance, providing a convenient method for constructing amide analogues. Notably, amino alcohols can be selectively transformed into the corresponding amides under the current standard conditions without interfering with the hydroxyl group.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Youcan Zhang, Hui-Qing Geng, Xiao-Feng Wu
Summary: The study presents a palladium-catalyzed four-component perfluoroalkylation/aminocarbonylation reaction, successfully synthesizing various β-perfluoroalkyl amides. The reaction system shows good compatibility with a wide range of substrates, including anilines, alkylamines, and demonstrates good functional-group tolerance and excellent chemoselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Analytical
Serkan Erdemir, Sait Malkondu, Mehmet Oguz
Summary: High levels of residual palladium can have serious negative health effects. A novel fluorescent probe has been designed for the rapid detection of palladium and carbon monoxide (CO). The probe can selectively detect Pd and CO with naked eyes and distinguish different species of Pd. The method has practical applications in drug residue and soil analysis, as well as bioimaging of Pd and CO concentration changes in cells.
Article
Chemistry, Inorganic & Nuclear
Lin Yang, Ai-Lin Guan, Zheng-Yang Xu, Zi-Jian Yao
Summary: A series of air- and moisture-stable cyclometalated ruthenium complexes based on N-heterocyclic ligands were prepared and showed excellent catalytic efficiency in phenoxy carbonylation of aryl halides. The catalytic system has a wide substrate range and mild reaction conditions, making it potential for industrial production.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ya-Hong Yao, Hui-Yi Yang, Ming Chen, Fei Wu, Xing-Xing Xu, Zheng-Hui Guan
Summary: A palladium-catalyzed asymmetric Markovnikov hydroaminocarbonylation reaction has been developed for the synthesis of 2-substituted propanamides with an alpha-stereocenter. The reaction employs a novel phosphoramidite ligand L16, shows high reactivity and selectivity, and operates through a palladium hydride pathway. The method allows for regio- and enantioselective synthesis of propanamides under ambient conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Inorganic & Nuclear
Axel Schulz, Alexander Hinz, Anne Rolke, Alexander Villinger, Ronald Wustrack
Summary: Phosphorus centered biradicaloids reacted with covalent and ionic azides, yielding different products. A Staudinger type reaction followed by PN bond rearrangement reactions was observed with covalent azides, while only diazides were formed with ionic azides. The new Staudinger type mechanism and the thermodynamics along different reaction paths were discussed based on DFT computations.
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE
(2021)
Article
Chemistry, Physical
Yasukazu Kobayashi, Shohei Tada, Masaru Kondo, Kakeru Fujiwara, Hiroshi Mizoguchi
Summary: Intermetallic YIr2 nanoparticles with a high surface area were prepared and found to possess high catalytic activity for the hydrogenation of cyclohexanone to cyclohexanol. This unique activity can be attributed to the charge transfer from Y to Ir, as supported by density functional theory calculations.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Xingzhuo Li, Zhenguo Wang, Wenjun Luo, Zixu Wang, Keshu Yin, Le Li
Summary: Conventional Staudinger reductions of aryl or bulky aliphatic azides are slow. Researchers have designed a new phosphine reagent that can efficiently mediate the reduction of these azides in both anhydrous and wet solvents.
