4441-56-9Relevant articles and documents
Electron donor compound and preparation method thereof, light emitting device and display device
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Paragraph 0063; 0119; 0120, (2021/02/06)
The invention relates to an electron donor compound, a light-emitting device, a preparation method of the light-emitting device and a display device. The electron donor compound has the following structural groups: each R1 independently selected from hydrogen, a trimethylsilyl group, a cyclohexyl group, a 3-pentyl group, a 4-(9,9'-spirobifluorene) group, a 2-(9,9'-diphenyl fluorene) group or a tetraphenyl vinyl group, wherein each R1 is not hydrogen at the same time. When the electron donor compound provided by the invention is used as an electron donor material to be applied to an interface heterojunction exciplex system, the original contact point of an electron donor and an electron acceptor is isolated by a non-hydrogen substituent, so that electrons and holes are separated in space, according to the invention, electrons of the electron acceptor layer can be prevented or hindered from easily moving into the electron donor layer, so that the electrification problem of quantum dots is avoided or relieved, and the efficiency and the service life of the light-emitting device are improved.
Hydrogenation of Borylated Arenes
Wollenburg, Marco,Moock, Daniel,Glorius, Frank
supporting information, p. 6549 - 6553 (2019/01/04)
A cis-selective hydrogenation of abundant aryl boronic acids and their derivatives catalyzed by rhodium cyclic (alkyl)(amino)carbene (Rh–CAAC) is reported. The reaction tolerates a variety of boron-protecting groups and provides direct access to a broad s
Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles
Ling, Liang,He, Yuan,Zhang, Xue,Luo, Meiming,Zeng, Xiaoming
, p. 6554 - 6558 (2019/04/17)
We herein report the hydrogenation of substituted aryl- and heteroaryl boronate esters for the selective synthesis of cis-substituted borylated cycloalkanes and saturated heterocycles. A cyclic (alkyl)(amino)carbene-ligated rhodium complex with two dimethyl groups at the ortho-alkyl scaffold of the carbene showed high reactivity in promoting the hydrogenation, thereby enabling the hydrogenation of (hetero)arenes with retention of the synthetically valuable boronate group. This process constitutes a clean, atom-economic, as well as chemo- and stereoselective route for the generation of cis-configured, diversely substituted borylated cycloalkanes and saturated heterocycles that are usually elusive and difficult to prepare.
Ambient-Pressure Asymmetric Preparation of S,S -DICHED, a C 2 -Symmetrical Director for Matteson Reactions
Bojaryn, Kevin,Hoffmann, Chris,Struth, Felix R.,Hirschh?user, Christoph
supporting information, p. 1092 - 1094 (2018/01/27)
A synthesis of S, S -DICHED (dicyclohexylethane-1,2-diol), a C 2 -symmetrical chiral director for Matteson homologations, is described. It relies on the insertion of lithiated S -2-cyclohexyloxirane into cyclohexylboronic acid pinacol ester and proceeds in three linear steps from readily available starting materials. No step requires chromatography or any specialized equipment.
SYNTHESIS OF BORONIC ESTERS AND BORONIC ACIDS USING GRIGNARD REAGENTS
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Paragraph 0102-0103; 0111, (2013/03/26)
Boronic esters and boronic acids are synthesized at ambient temperature in an ethereal solvent by the reaction of Grignard reagents with a boron-containing substrate. The boron-containing substrate may be a boronic ester such as pinacolborane, neopentylglycolborane, or a dialkylaminoborane compound such as diisopropylaminoborane. The Grignard reagents may be preformed or generated from an alkyl, alkenyl, aryl, arylalkyl, heteroaryl, vinyl, or allyl halide compound and Mg°. When the boron-containing substrate is a boronic ester, the reactions generally proceed at room temperature without added base in about 1 to 3 hours to form a boronic ester compound. When the boron-containing substrate is a dialkylaminoborane compound, the reactions generally proceed to completion at 0°C in about 1 hour to form a boronic acid compound.
Organotrifluoroborate hydrolysis: Boronic acid release mechanism and an acid-base paradox in cross-coupling
Lennox, Alastair J. J.,Lloyd-Jones, Guy C.
, p. 7431 - 7441 (2012/06/16)
The hydrolysis of potassium organotrifluoroborate (RBF3K) reagents to the corresponding boronic acids (RB(OH)2) has been studied in the context of their application in Suzuki-Miyaura coupling. The "slow release" strategy in such SM couplings is only viable if there is an appropriate gearing of the hydrolysis rate of the RBF3K reagent with the rate of catalytic turnover. In such cases, the boronic acid RB(OH)2 does not substantially accumulate, thereby minimizing side reactions such as oxidative homocoupling and protodeboronation. The study reveals that the hydrolysis rates (THF, H2O, Cs2CO 3, 55 °C) depend on a number of variables, resulting in complex solvolytic profiles with some RBF3K reagents. For example, those based on p-F-phenyl, naphthyl, furyl, and benzyl moieties are found to require acid catalysis for efficient hydrolysis. This acid-base paradox assures their slow hydrolysis under basic Suzuki-Miyaura coupling conditions. However, partial phase-splitting of the THF/H2O induced by the Cs2CO 3, resulting in a lower pH in the bulk medium, causes the reaction vessel shape, material, size, and stirring rate to have a profound impact on the hydrolysis profile. In contrast, reagents bearing, for example, isopropyl, β-styryl, and anisyl moieties undergo efficient "direct" hydrolysis, resulting in fast release of the boronic acid while reagents bearing, for example, alkynyl or nitrophenyl moieties, hydrolyze extremely slowly. Analysis of B-F bond lengths (DFT) in the intermediate difluoroborane, or the Swain-Lupton resonance parameter (R) of the R group in RBF3K, allows an a priori evaluation of whether an RBF3K reagent will likely engender "fast", "slow", or "very slow" hydrolysis. An exception to this correlation was found with vinyl-BF 3K, this reagent being sufficiently hydrophilic to partition substantially into the predominantly aqueous minor biphase, where it is rapidly hydrolyzed.
Reaction of grignard reagents with diisopropylaminoborane. Synthesis of alkyl, aryl, heteroaryl and allyl boronic acids from organo(diisopropyl)- aminoborane by a simple hydrolysis
Bailey, Christopher L.,Murphy, Chris L.,Clary, Jacob W.,Eagon, Scott,Gould, Naomi,Singaram, Bakthan
, p. 331 - 341 (2013/08/23)
Diisopropylaminoborane (BH2-N(iPr)2) is prepared by reacting lithium diisopropylaminoborohydride (iPr-LAB) with trimethylsilyl chloride (TMSCl). Aliphatic, aromatic, and heteroaromatic (diisopropylamino) boranes are readily synthesiz
Dichloroborane-dioxane: An exceptional reagent for the preparation of alkenyl- and alkylboronic acids
Josyula, Kanth V. B.,Gao, Peng,Hewitt, Chris
, p. 7789 - 7792 (2007/10/03)
Terminal alkynes and alkenes were conveniently hydroborated to the corresponding alkenyl- and alkyldichloroboranes using dichloroborane-dioxane in dichloromethane. These dichloroboranes were hydrolyzed by water to the corresponding alkenyl- and alkylboron
Reactions of phosphonates with organohaloboranes: New route to molecular borophosphonates
Mortier, Jacques
, p. 4266 - 4275 (2008/10/08)
Phosphonates RPO(OR′)2 (R = Me, R′ = Et (1); R = CH2Ph, R′ = Et (2); R = CH double bond CH2, R′ = Et (3); R = CH2-CH double bond CH2, R′ = Me (4); R = CH2N3, R′ = Et (5)) react with CyBCl2 (6; Cy = C6H11) in a 1:1 molar ratio in toluene at -30 °C to form the primary adducts CyBCl2·O double bond PR(OR′)2 (7-11). These products undergo a thermally induced bis-chlorodealkylation with the formation of mixtures of oligomers [-O-PR(O-)-O-BCy(O-)]n (22-26) having isovalent P-O-B groupings. Under electron impact mass spectral conditions, the ions [RPO3BCy]4-Cy, which may be attributed to tetramers [RPO3BCy]4 (22′-26′), are detected. Compounds 22′-26′ presumably possess a central cubic M4O12P4 framework that is analogous to those found in alumino- and gallophosphate materials. NMR monitoring shows that [CyBCl(μ2-O)2PR(OR′)]2 (12-16) are formed as intermediates in these reactions. These unstable dimers 12-16 possess a cyclic core analogous to the single-four-ring (4R) secondary building units (SBUs) found in zeolites and phosphate molecular sieves. Hydrolysis of 12-16 and 22-26 with methanol at 30 °C gave respectively RPO(OH)(OR′) (17-21) and RPO(OH)2 (27-31). NMR monitoring reveals that the cyclic dimer [Me2B(μ2-O)2P(CH2Ph)(OEt)]2 (35a) is the primary adduct in the reaction of PhCH2PO(OEt)2 (2) with Me2BBr (34). Heating or prolonged storage at room temperature leads to a mixture of 35a, cyclic borophosphonate Me2BC(μ2-O)2P(CH2Ph)(OEt) (35b), and the mixed anhydride of benzylphosphonic acid and dimethylborinic acid (35c).
Organoboranes. LI. Convenient procedures for the recovery of pinanediol in asymmetric synthesis via one-carbon homologation of boronic esters
Brown, Herbert C.,Rangaishenvi, Milind V.
, p. 15 - 30 (2007/10/02)
Matteson's asymmetric synthesis via a one-carbon homologation of the pinanediol boronic esters with (dichloromethyl)litihium at -100 deg C results in the insertion of a chloromethyl group into the carbon-carbon bond with > 99percent diastereoselectivity.This procedure makes possible the asymmetric synthesis of the chiral moiety, RR'CH*B(OR'')2, providing an alternative route to chiral hydroboration for these valuable chiral intermediates.Unfortunately, this method suffers from the remarkable difficulty encountered in the recovery of the pinanediol chiral auxiliary, making this asymmetric synthesis impractical.Fortunately, a systematic study of the problem has uncovered convenient procedures for the recovery of pinanediol from pianendiol boronate esters
