14676-52-9Relevant academic research and scientific papers
Tunable Single and Double γ-C?H Arylation of Phenylacetamides Directed by o-Aminophenols
Tu, Zhi,Du, Yi,Cao, Xiaoji,Liu, Yunyun
, p. 4989 - 4997 (2019)
The cheap and easily available o-aminophenols (OAPs) have been identified as practical directing component for the Pd-catalyzed aromatic γ-C?H bond arylation of phenylacetamides. Notably, the selective single and double arylation of the C?H bond(s) in the
Primary Amide Directed Regioselective ortho-C-H-Arylation of (Aryl)Acetamides
Jaiswal, Yogesh,Kumar, Yogesh,Thakur, Rima,Pal, Jagannath,Subramanian, Ranga,Kumar, Amit
, p. 12499 - 12505 (2016)
An efficient and regioselective palladium(II)-catalyzed primary acetamide assisted ortho arylation of arylacetamide has been discovered. This is the first report where functionalizable primary acetamide (?CH2CONH2) is used as a directing group for C(sp2)-H activation/cross-coupling reactions, circumventing the extra steps of installation and subsequent removal of the directing groups. The synthetic utility of this transformation is demonstrated through the scale-up synthesis. In addition, the primary acetamide can be manipulated into synthetically important derivatives such as nitriles and carboxylic acids.
Magnetic nanoparticles as an orthogonal support of polymer resins: Applications to solid-phase Suzuki cross-coupling reactions
Zheng, Yan,Stevens, Philip D.,Gao, Yong
, p. 537 - 542 (2006)
Most of the reactants immobilized on conventional solid-phase resins are buried inside the interiors of lightly cross-linked polystyrene beads. An orthogonal support of solid-phase resins needs to be small enough to penetrate the interpolymeric chain spaces of a swollen resin to reach reaction sites. In this paper, we report the use of magnetic nanoparticles (～4 nm) as an orthogonal matrix to assist solid-phase reactions. A magnetic nanoparticle-supported homogeneous Pd catalyst was employed for promoting the Suzuki cross-coupling of an aryl halide on resins and an excessive arylboronic acid in solution. The workup separating three components (the catalyst, product, and remaining arylborate) is a chromatography-free process. The Pd catalyst was magnetically isolated and recycled from the reaction mixture by applying an external magnetic field. Then, a filtration process was followed to recover the excess borate reagent from the resins/product. Our work here presents the first example of an orthogonal matrix of solid-phase resins and shows the promise of employing nanomaterials in organic synthesis.
Palladium-catalyzed intramolecular aromatic C-H acylation of 2-arylbenzoyl fluorides
Hayakawa, Kazuki,Ikai, Kana,Ogiwara, Yohei,Sakai, Norio,Sakurai, Yuka
, p. 1882 - 1893 (2021/08/13)
The catalytic intramolecular cyclization of acyl fluorides using a Pd(OAc)2/PCy3 system is described. A wide range of 2-arylbenzoyl fluoride derivatives can be used as fluorenone precursors and the reaction proceeds via an intramolecular coupling between aromatic C-H bonds with acyl C-F bonds. The reaction can be applied to the synthesis of indenofluorenedione derivatives and to the construction of other molecules with fivemembered rings.
Hydroxyl-substituted phenanthrene derivative synthesis method
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Paragraph 0033-0036, (2019/04/17)
The invention relates to a hydroxyl-substituted phenanthrene derivative synthesis method, which includes taking a 2-carboxymethyl biphenyl compound as a raw material; and reacting under the action ofa catalyst to obtain a hydroxyl-substituted phenanthrene derivative, wherein the catalyst comprises one or two of trifluoromethanesulfonic acid or phosphorus pentoxide. Compared with the prior art, the synthesis method has the advantages of the cheap and easily-available catalyst, good universality of functional groups, simple and convenient operation, short reaction time, high reaction yield, mild reaction conditions and the like.
Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts
Liao, Li-Li,Cao, Guang-Mei,Ye, Jian-Heng,Sun, Guo-Quan,Zhou, Wen-Jun,Gui, Yong-Yuan,Yan, Si-Shun,Shen, Guo,Yu, Da-Gang
, p. 17338 - 17342 (2019/01/04)
Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.
A General, Activator-Free Palladium-Catalyzed Synthesis of Arylacetic and Benzoic Acids from Formic Acid
Wang, Lin,Neumann, Helfried,Beller, Matthias
supporting information, p. 6910 - 6914 (2018/06/04)
A new catalyst for the carboxylative synthesis of arylacetic and benzoic acids using formic acid (HCOOH) as the CO surrogate was developed. In an improvement over previous work, CO is generated in situ without the need for any additional activators. Key to success was the use of a specific system consisting of palladium acetate and 1,2-bis((tert-butyl(2-pyridinyl)phosphinyl)methyl)benzene. The generality of this method is demonstrated by the synthesis of more than 30 carboxylic acids, including non-steroidal anti-inflammatory drugs (NSAIDs), under mild conditions in good yields.
BIPHENYLACETAMIDE DERIVATIVE
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Page/Page column 12, (2011/10/04)
The present invention provides a compound of formula (I) or a salt thereof, wherein R1, R2 and R3 are independently selected from the group consisting of hydrogen atom, fluorine atom, chlorine atom, bromine atom, C1-6 alkyl, C1-6 alkoxy substituted with fluorine atom, and others; R4 and R5 are independently selected from the group consisting of hydrogen atom, fluorine atom, chlorine atom, C1-6 alkyl, C1-6 alkoxy substituted with fluorine atom, and others; R6 and R7 are independently selected from the group consisting of hydrogen atom, fluorine atom, methyl, ethyl, hydroxy group, and others; and R8 and R9 are independently selected from the group consisting of hydrogen atom, C1-6 alkyl, and others, which is useful as an agent for treating or preventing various types of epilepsy including partial seizures and/or generalized seizures.
NANO-REAGENTS WITH COOPERATIVE CATALYSIS AND THEIR USES IN MULTIPLE PHASE REACTIONS
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Page/Page column 12-13; sheet 11/11, (2011/08/08)
Nano-reagents with catalytic activity are provided herein. The nanocatalyst comprises at least one amino acid attached to a nanoparticle, wherein the reactive side chain of the amino acid catalyzes a chemical or biological reaction. Methods of using these nano-reagents to catalyze reactions in solution or in multiple phases are also provided, as are methods of making these nanocatalysts.
Palladium charcoal-catalyzed, ligandless Suzuki reaction by using tetraarylborates in water
Lu, Gang,Franzén, Robert,Zhang, Qian,Xu, Youjun
, p. 4255 - 4259 (2007/10/03)
In water and without using any ligand, palladium charcoal-catalyzed Suzuki coupling reaction of tetraarylborates with aryl bromides could be achieved in excellent yield. A concise mechanism consisting of four catalytic cycles is depicted in this paper.
