114772-33-7Relevant articles and documents
Very efficient and broad-in-scope palladium-catalyzed Hiyama cross-coupling. the role of water and copper(I) salts
Traficante, Carla I.,Mata, Ernesto G.,Delpiccolo, Carina M. L.
, p. 26796 - 26800 (2015)
A very high-yielding Pd-catalyzed cross-coupling between aryl halides and aryl(trialkoxy)silanes is achieved in the presence of Cu(i) and a measured amount of water. This novel methodology is useful for the generation of a wide range of biaryls, particularly non-para substituted derivatives, which are usually less reported.
Synthesis of biaryls via nickel-catalyzed cross-coupling reaction of arylboronic acids and aryl mesylates
Ueda, Masato,Saitoh, Atsushi,Oh-tani, Saori,Miyaura, Norio
, p. 13079 - 13086 (1998)
The cross-coupling reaction of arylboronic acids (1.3 equivs) with aryl methanesulfonates was carried out in the presence of a nickel(0) catalyst (3 mol%) and K3PO4·nH2O (3 equivs). The use of toluene as the solvent and the nickel(0)-dppf catalyst prepared from NiCl2(dppf) plus dppf with BuLi were recognized to be the most efficient to achieve both high yields and high selectivity. The reaction can be applied to various electron-deficient and - rich aryl methanesulfonates to give high yields.
Identification of optimal anion spacing for anti-HIV activity in a series of cosalane tetracarboxylates
Paul, Gitendra C.,De Clercq, Erik,Pannecouque, Christophe,Witvrouw, Myriam,Loftus, Tracy L.,Turpin, Jim A.,Buckheit Jr., Robert W.,Cushman, Mark
, p. 2149 - 2152 (2000)
The binding of the anti-HIV agent cosalane to CD4 is thought to involve ionic interactions of negatively charged carboxylates of the ligand with positively charged residues on the surface of the protein. An investigation of the optimal anion distances for anti-HIV activity in a series of cosalane tetracarboxylate analogues has been completed, and maximal activity results when the two proximal and the two distal carboxylates are separated by eight atoms. (C) 2000 Elsevier Science Ltd.
A Highly Efficient Monophosphine Ligand for Parts per Million Levels Pd-Catalyzed Suzuki–Miyaura Coupling of (Hetero)Aryl Chlorides
Choy, Pui Ying,Yuen, On Ying,Leung, Man Pan,Chow, Wing Kin,Kwong, Fuk Yee
, p. 2846 - 2853 (2020)
A new indolylphosphine WK-phos has been synthesized for Pd-catalyzed Suzuki–Miyaura coupling of (hetero)aryl chlorides with (alkyl)arylboronic acids. Comprising this newly developed ligand with palladium(II) acetate, the resulting catalyst system was found to be highly effective in facilitating the reaction even when the catalyst loading reaches parts per million levels (e.g. 10 ppm). These examples represent one of the lowest catalyst loadings reported to date of employing monophosphine (e.g. Ar-PCy2) for Suzuki–Miyaura reactions. The ligand geometry has also been well-characterized by single-crystal X-ray crystallography.
Direct Synthesis of Ketones from Methyl Esters by Nickel-Catalyzed Suzuki–Miyaura Coupling
Daneshfar, Omid,Hong, Xin,Houk, Kendall N.,Newman, Stephen G.,Xie, Pei-Pei,Zheng, Yan-Long
, p. 13476 - 13483 (2021)
The direct conversion of alkyl esters to ketones has been hindered by the sluggish reactivity of the starting materials and the susceptibility of the product towards subsequent nucleophilic attack. We have now achieved a cross-coupling approach to this transformation using nickel, a bulky N-heterocyclic carbene ligand, and alkyl organoboron coupling partners. 65 alkyl ketones bearing diverse functional groups and heterocyclic scaffolds have been synthesized with this method. Catalyst-controlled chemoselectivity is observed for C(acyl)?O bond activation of multi-functional substrates bearing other bonds prone to cleavage by Ni, including aryl ether, aryl fluoride, and N-Ph amide functional groups. Density functional theory calculations provide mechanistic support for a Ni0/NiII catalytic cycle and demonstrate how stabilizing non-covalent interactions between the bulky catalyst and substrate are critical for the reaction's success.
para-Selective arylation and alkenylation of monosubstituted arenes using thianthreneS-oxide as a transient mediator
Chen, Xiao-Yue,Nie, Xiao-Xue,Wu, Yichen,Wang, Peng
, p. 5058 - 5061 (2020/05/18)
Using thianthreneS-oxide (TTSO) as a transient mediator,para-arylation and alkenylation of mono-substituted arenes have been demonstratedviaapara-selective thianthrenation/Pd-catalyzed thio-Suzuki-Miyaura coupling sequence under mild conditions. This reaction features a broad substrate scope, and functional group and heterocycle tolerance. The versatility of this approach was further demonstrated by late-stage functionalization of complex bioactive scaffolds, and direct synthesis of some pharmaceuticals, including Tetriprofen, Ibuprofen, Bifonazole, and LJ570.
Preparation method of para-substituted aryl compound
-
, (2020/06/09)
The invention discloses a preparation method of a para-substituted aryl compound shown as a formula (I) which is described in the specfication. The preparation method is characterized by comprising the following step of: subjecting an aryl sulfonium salt shown as a formula (II) which is described in the specfication and boride to a coupling reaction in a solvent in an inert atmosphere under the action of alkali and a palladium catalyst to obtain the para-substituted aryl compound. According to the method, mono-substituted aromatic hydrocarbon is taken as a substrate, the aryl sulfonium salt isconstructed in situ, and the palladium catalyst catalyzes the aryl sulfonium salt constructed in situ to undergo the Suzuki-Miyaura coupling reaction, so a mono-substituted aromatic hydrocarbon para-arylation or alkenylation product is constructed quickly and efficiently. The method is mild in conditions, high in substrate universality and wide in tolerance of a heterocyclic coupling substrate.
Phosphine ligand for indole skeleton as well as preparation method and application of phosphine ligand
-
Paragraph 0212; 0215; 0221-0226, (2017/12/30)
The invention provides a phosphine ligand for a 3-(disubstituted phosphino)-1-alkyl-2-substituted phenyl-indole skeleton as well as a preparation method and application of the phosphine ligand. The structure of the phosphine ligand for the 3-(disubstituted phosphino)-1-alkyl-2-substituted phenyl-indole skeleton is shown as the following formula I: (shown in the description), wherein Z is carbon or nitrogen, R is alkyl, substituted alkyl, olefin, aryl or fluorine, R1 is alkyl, substituted alkyl or aryl, R2 is alkyl, substituted alkyl or fluorine, and R3 is alkyl, substituted alkyl or aryl.
An Indefinitely Air-Stable σ-NiII Precatalyst for Quantitative Cross-Coupling of Unreactive Aryl Halides and Mesylates with Aryl Neopentylglycolboronates
Malineni, Jagadeesh,Jezorek, Ryan L.,Zhang, Na,Percec, Virgil
supporting information, p. 2795 - 2807 (2016/08/31)
Three classes of Ni precatalysts based on π-NiII, π-Ni0 and σ-NiII complexes have been elaborated and employed in different laboratories for the functionalization and cross-coupling of otherwise inert aryl C-O, C-Cl, and C-F electrophiles. Various Ni precatalysts, ligands, boron sources, and reaction conditions that were developed in various research groups, necessitated the selection of the most suitable conditions for desired cross-coupling partners. Here a universal, bench-stable, easily prepared NiIICl(1-naphthyl)(PCy3)2/PCy3 σ-complex, for efficient and quantitative cross-coupling of aryl chlorides, bromides, iodides, mesylates, and fluorides with aryl neopentylglycolboronates is reported. This precatalyst will most probably help to advance the applications of Ni catalysis in organic, supramolecular, and macromolecular synthesis and will provide an easier access to the selection of reaction conditions for various transformations.
New telmisartan-derived PPARγ agonists: Impact of the 3D-binding mode on the pharmacological profile
Obermoser, Victoria,Urban, Margarethe E.,Murgueitio, Manuela S.,Wolber, Gerhard,Kintscher, Ulrich,Gust, Ronald
supporting information, p. 138 - 152 (2016/08/30)
In previous studies, the 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid was identified as pharmacophoric core for PPARγ activation. In this structure-activity relationship study the C2-alkyl chain was elongated and the 2-COOH group was changed to a carbamide/carbonitrile or shifted to the 3- or 4-position. Furthermore, the benzo[d]imidazole was exchanged by 2,3-dihydrobenzo[d]thiazole or 1H-indole. C2-propyl derivatives showed the profile of partial agonists, while elongation of the C2-chain to that of an n-heptyl group or a 4-COOH shift changed the pharmacological profile to that of a potent full agonist. This finding can be explained by binding to the LBD in different ligand conformations. Two anchoring points (Tyr473 and Arg288) exist in the LBD, which have to be contacted to achieve receptor activation. In a crystal violet chemosensitivity assay using COS-7?cells and LNCaP cells expressing PPARγ only the carbamide derivatives influenced the cell growth, independently on the presence of the PPARγ. Therefore, receptor mediated cytotoxicity can be excluded.
