128376-64-7Relevant articles and documents
Photocatalytic C–X borylation of aryl halides by hierarchical SiC nanowire-supported Pd nanoparticles
Jiao, Zhi-Feng,Zhao, Ji-Xiao,Guo, Xiao-Ning,Guo, Xiang-Yun
, p. 357 - 363 (2020)
Hierarchical SiC nanowire-supported Pd nanoparticles showed high photocatalytic activity for the C-X (X = Br, I) borylation of aryl halides at 30 °C. The SiC/Pd Mott-Schottky contact enhances the rapid transfer of the photogenerated electrons from SiC to the Pd nanoparticles. As a result, the concentrated energetic electrons in the Pd nanoparticles can facilitate the cleavage of C-I or C-Br bonds, which normally requires high-temperature thermal processes. We show that the present Pd/SiC photocatalyst is capable of catalyzing the transformation of a large variety of aryl halides to their corresponding boronate esters under visible light irradiation, with excellent yields.
Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water
Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg
, p. 1842 - 1851 (2018)
A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
Use of in situ isopropoxide protection in the metal-halogen exchange of arylboronates
Jiang, Qin,Ryan, Meagan,Zhichkin, Paul
, p. 6618 - 6620 (2007)
(Chemical Equation Presented) Isopropoxide protection of arylboronates allowed their use in metal-halogen exchange reactions. The isopropoxide- protected borate species were obtained from a boronate or in situ from dibromoarenes. meta- and para-dibromoare
Behavior of Supramolecular Assemblies of Radiometal-Filled and Fluorescent Carbon Nanocapsules In?Vitro and In?Vivo
Ge, Haobo,Riss, Patrick J.,Mirabello, Vincenzo,Calatayud, David G.,Flower, Stephen E.,Arrowsmith, Rory L.,Fryer, Tim D.,Hong, Young,Sawiak, Steve,Jacobs, Robert M.J.,Botchway, Stanley W.,Tyrrell, Rex M.,James, Tony D.,Fossey, John S.,Dilworth, Jonathan R.,Aigbirhio, Franklin I.,Pascu, Sofia I.
, p. 437 - 460 (2017)
Hybrid materials based on supramolecularly assembled single-walled carbon nanotubes (SWNTs) are generated for positron emission tomography (PET), magnetic resonance imaging, and fluorescence imaging. The all-in-one imaging probe allows quantitative imaging from subcellular resolution to whole tissue regions. The SWNTs can be exposed to aqueous solutions of non-radioactive and radioactive metal salts in the presence of fullerenes and β-D-glucan. Encapsulating 64Cu ions achieves a minimum of 69% incorporation of radiochemical. The results suggest that this method can be extended to other metal ions of medical relevance, such as zirconium(IV)-89 or rhenium(VII)-188, which are used for medical imaging or radiotherapy, respectively. The in vivo uptake of 64Cu(II)@SWNT@β-D-glucan in Wistar rats allows the investigation of organ biodistribution by microPET. Radioactivity rapidly accumulates predominantly in the lungs and myocardium with peak uptakes of 4.8 ± 0.9 standardized uptake value. Furthermore, such materials are fully traceable in cells by multiphoton fluorescence lifetime imaging with near-infrared excitation (910 nm).
Nitro-substituted stilbeneboronate pinacol esters and their fluoro-adducts. Fluoride ion induced polarity enhancement of arylboronate esters
Oehlke, Alexander,Auer, Alexander A.,Jahre, Ina,Walfort, Bernhard,Rueffer, Tobias,Zoufala, Petra,Lang, Heinrich,Spange, Stefan
, p. 4328 - 4339 (2007)
(Chemical Equation Presented) A series of stilbeneboronate pinacol cyclic esters, containing none to three nitro groups, have been synthesized by various olefination reactions and characterized by X-ray single-crystal structure analysis. A stilbeneboronat
Pd(II) Complexes with Chelating Phosphinoferrocene Diaminocarbene Ligands: Synthesis, Characterization, and Catalytic Use in Pd-Catalyzed Borylation of Aryl Bromides
?koch, Karel,Schulz, Ji?í,Císa?ová, Ivana,?těpni?ka, Petr
, p. 3060 - 3073 (2019)
We developed a novel, straightforward route toward Pd(II)-aminocarbene complexes bearing a P-chelating phosphinoferrocenyl substituent based on a three-component reaction of 1′-(diphenylphosphino)-1-isocyanoferrocene (1) with [PdCl2(cod)] (cod = cycloocta-1,5-diene) and nucleophilic amines. Depending on the type of the amine, the reaction produced acyclic diaminocarbenes and their saturated (imidazolin-2-ylidene) and unsaturated (imidazol-2-ylidene) cyclic counterparts (NHCs). Using (S)-2-(chloromethyl)pyrrolidine as the nucleophile, this method afforded a separable pair of stable diastereomeric bicyclic imidazolin-2-ylidene carbenes with different configurations of the planar-chiral ferrocene unit. The prepared P-chelating carbenes were characterized using spectroscopic methods, X-ray crystallography, and DFT methods. The last were used to explain the formation of isomeric open diaminocarbenes featuring NHR groups at the wing-tip position, trends in Pd-Cl bond lengths reflecting similar trans influences of the particular carbene and phosphine donors, and the results from cyclic voltammetric measurements. Furthermore, the carbenes were used as defined (pre)catalysts in Miyaura borylation of aryl bromides with bis(pinacolato)diboron. When applying the optimized catalytic system (1 mol % Pd catalyst, KOAc as the base, 2-propanol, 85 °C), this reaction produced a range of simple and substituted arylboronate pinacol esters in high yield and without biaryl side products.
Isophorone-boronate ester: A simple chemosensor for optical detection of fluoride anion
Ranjith Kumar, Jakku,Rami Reddy, Eda,Trivedi, Rajiv,Vardhaman, Anil Kumar,Giribabu, Lingamallu,Mirzadeh, Nedaossadat,Bhargava, Suresh K.
, (2019)
A highly selective isophorone-boronate ester based chemosensor, (1), having a dicyanovinyl moiety as a convenient colorimetric probe, has been designed. Different types of anionic analyte such as CH3COO?, ClO4?,
1-[5-(4,5-Dimethyl-1,3,2-dioxaboro-lan-2-yl)thio-phen-2-yl]ethanone and 4-(4,4,5,5-tetra-methyl-1,3,2-dioxa-borolan-2-yl)benzaldehyde
Urdaneta, Neudo,Nuez, Jess,Gonzalez, Teresa,Briceo, Alexander
, p. o213-o215 (2012)
In both title compounds, C10H13BO3S, (I), and C13H17BO3, (II), the mol-ecules adopt nearly planar conformations. The crystal packing of (I) consists of a supra-molecular two-dimensional network with a herringbone-like topology formed by self assembly of centrosymmetric pairs of mol-ecules linked via dipole-dipole inter-actions. The crystal structure of (II) consists of a supra-molecular two-dimensional network built up from centrosymmetric pairs of mol-ecules via π-π inter-actions. These pairs of mol-ecules are self-organized in an offset fashion related by a symmetry centre, generating supra-molecular ribbons running along the [101] direction. Neighbouring ribbons are stacked via complementary van der Waals and hydro-phobic methyl-methyl inter-actions.
Facile and economical Miyaura borylation and one-pot Suzuki–Miyaura cross-coupling reaction
Boontiem, Phongsakorn,Kiatisevi, Supavadee
, (2020)
Facile and economical method for Miyaura borylation reaction between B2pin2 and aryl bromides is reported. The catalytic system containing 2 mol% PdCl2(PPh3)2 and KOAc serves to enable borylations to occur under solvent-free and atmospheric conditions. The developed protocol can be applied to synthesize symmetrical and unsymmetrical biaryls via one-pot two-step Suzuki–Miyaura cross-coupling reaction and also offers the up-scalability.
Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis
García Manche?o, Olga,Kuhlmann, Jan H.,Pérez-Aguilar, María Carmen,Piekarski, Dariusz G.,Uygur, Mustafa
supporting information, p. 3392 - 3399 (2021/05/21)
A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.
Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage
Balakrishnan, Venkadesh,Murugesan, Vetrivelan,Chindan, Bincy,Rasappan, Ramesh
supporting information, p. 1333 - 1338 (2021/02/20)
Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.
