110180-68-2Relevant academic research and scientific papers
Amine-borane complexes: Air- and moisture-stable partners for palladium-catalyzed borylation of aryl bromides and chlorides
Guerrand, Hélène D. S.,Vaultier, Michel,Pinet, Sandra,Pucheault, Mathieu
, p. 1167 - 1174 (2015)
A method for using amine-borane complexes directly in palladium catalyzed borylation has been developed. The reaction proceeds through the sequential formation of a boronium species followed by deprotonation leading to the aminoborane. This reagent is then directly used in the borylation process leading, after work-up, to various boronic acid derivatives. The reaction was applied to (hetero)aryl triflates, iodides, bromides and chlorides.
Method for preparing aminoarylborane compounds or derivatives thereof
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, (2015/06/17)
The present invention provides a process for the preparation of aminoarylborane compounds and derivatives thereof comprising a step of arylation by reacting an aryl chloride with an aminoborane compound in the presence of a catalytic system. Typically, th
COMPOUND AND ORGANIC ELECTROLUMINESCENE ELEMENT
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Paragraph 0230; 0232, (2016/10/10)
The present invention provides a compound represented by chemical formula (1-1) and containing a diaminobiphenyl group disposed between two dibenzothiophenes or two dibenzofurans. In chemical formula (1-1), two Aandprime;s are the same as each other, and are oxygen or sulfur. Xa and Xb each represent independently hydrogen, or any one of (a) to (c) below. When any one of Xa and Xb is hydrogen, the other is anyone else other than hydrogen. Ya and Yb each represent independently (d) below. (a) is a straight-chain or cyclic alkyl group or alkoxy group which may have a substituent. The substituent of (a) the straight-chain or cyclic alkyl group or alkoxy group which may have a substituent is any one of an alkyl group, a halogen group, an amino group, a nitro group, and a cyano group. (b) and (d) are an aromatic cyclic group which may have a substituent. The substituent of (b) and (d) the aromatic cyclic group which may have a substituent is any one of an alkyl group, a halogen group, an amino group, a nitro group, and a cyano group. The aromatic cyclic group of (b) and (d) is an aromatic hydrocarbon group or an aromatic heterocyclic group. (c) is any one of a halogen group, an amino group, a nitro group, and a cyano group.COPYRIGHT KIPO 2015
HOLE TRANSPORTING MATERIAL
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Paragraph 0133-0134, (2017/03/17)
PROBLEM TO BE SOLVED: To provide a novel compound that has a wide bandgap, is excellent in electrical stability, thermal stability and charge transporting performance and can also be used for hole transporting layers of an organic EL element, and to provide a material that gives good quality of film obtained by applying to form a film and can be insolubilized after forming the film. SOLUTION: There is provided a compound represented by following formula (1), which has a wide bandgap, is excellent in electrical stability, thermal stability and charge transporting performance and can be used for hole transporting layers of an organic EL element. In the formula, at least one of X1 to X6 represents a polymerizable functional group; n represents an integer of 2 to 8; R represents H, an alkyl group or the like; Z1 and Z2 represent an optionally substituted aromatic cyclic group; substituents of the aromatic cyclic group in the Z1 and the Z2 include a linear or cyclic alkyl group, alkoxy group, halogen group, amino group, nitro group or cyano group. COPYRIGHT: (C)2015,JPO&INPIT
Mn-catalyzed aromatic C-H alkenylation with terminal alkynes
Zhou, Bingwei,Chen, Hui,Wang, Congyang
supporting information, p. 1264 - 1267 (2013/03/14)
The first manganese-catalyzed aromatic C-H alkenylation with terminal alkynes is described. The procedure features an operationally simple catalyst system containing commercially available MnBr(CO)5 and dicyclohexylamine (Cy2NH). The reaction occurs readily in a highly chemo-, regio-, and stereoselective manner delivering anti-Markovnikov E-configured olefins in high yields. Experimental study and DFT calculations reveal that (1) the reaction is initiated by a C-H activation step via the cooperation of manganese and base; (2) manganacycle and alkynylmanganese species are the key reaction intermediates; and (3) the ligand-to-ligand H-transfer and alkynyl-assisted C-H activation are the key steps rendering the reaction catalytic in manganese.
Synthesis of phenylboronic acids in continuous flow by means of a multijet oscillating disc reactor system operating at cryogenic temperatures
Sleveland, Dagfinn,Bjorsvik, Hans-Rene
experimental part, p. 1121 - 1130 (2012/08/27)
A multijet oscillating disk (MJOD) millireactor system suitable for operating at cryogenic temperatures has been developed, assembled, and investigated. This new reactor system (cryoMJOD) was realized with the purpose to prepare various phenylboronic acids in a continuous two (three)-step telescoped synthetic process at temperatures in the interval -50 to -75 °C. In this process, n-butyllithium was reacted with a phenylbromide to provide the corresponding phenyllithium derivative, whereupon a borate was added under the formation of target product phenylboronic acid in good selectivity and medium-to-good yield (50-75%). These results were competitive with results previously revealed in the literature. The residence times of the telescoped two-step process were considerably shorter compared to those of batch mode operations for the identical syntheses. The flow process was optimized by means of statistical experimental design and multivariate regression, upon which the process was utilized for the production of a series of phenylboronic acid derivatives, all in medium-to-good yield. One of the substrates, 4-methoxyphenylboronic acid, was submitted for throughput improvements, resulting in a process with capability to produce the product phenylboronic acid in a quantity of 2.0 kg × day-1.
Functionalization of (2S)-Isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4- ones by a Suzuki-Miyaura Cross-Coupling Reaction Using Aryltrifluoroborate Salts: Convenient Enantioselective Preparation of α-Substituted β-Amino Acids
Stefani, Helio A.,Amaral, Monica F. Z. J.,Reyes-Rangel, Gloria,Vargas-Caporali, Jorge,Juaristi, Eusebio
experimental part, p. 6393 - 6403 (2011/02/21)
A simple protocol for the Pd(OAc)2-catalyzed cross-coupling reaction of 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones with potassium aryltrifluoroborates was developed. The reaction is performed at 110°C with a ligand-free catalyst. In all cases, complete conversion of the 1-benzoyl-(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-onesand aryltrifluoroborates into the C-C coupling products was observed within 30-360 min. It is noteworthy that a largevariety of groups present in the potassium aryltrifluoroborates (-CF3, -OMe, -SEt, -CN, -CHO, -Cl, -Cbz, -NCbz,-OH, -CO2H) could be tolerated. Hydrogenation of the endocyclic double bonds in the Suzuki-Miyaura products followed by acid hydrolysis afforded highly enantioenrichedα-aryl-substituted β-amino acids. We present a general approach for the synthesis of (2S)-isopropyl-5-aryl-2,3- dihydro-4(H)-pyrimidin-4-ones by Suzuki-Miyaura reaction of aryltrifluoroborate salts with(2S)-isopropyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones in the presence of a palladium catalyst and a base. The arylated compounds were transformed into enantioenriched α-aryl-substituted β-amino acids. Copyright
