cas 914675-52-8, Biphenyl-2-boronic acid pinaco

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Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis
Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.
Firth, James D.,Hammarback, L. Anders,Burden, Thomas J.,Eastwood, Jonathan B.,Donald, James R.,Horbaczewskyj, Chris S.,McRobie, Matthew T.,Tramaseur, Adam,Clark, Ian P.,Towrie, Michael,Robinson, Alan,Krieger, Jean-Philippe,Lynam, Jason M.,Fairlamb, Ian J. S.
supporting information
p. 3979 - 3985
(2021/02/03)

Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates
Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.
Cai, Mingzhong,Huang, Bin,Luo, Chengkai,Xu, Caifeng
(2021/12/02)

Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation
The conversion of silyloxyarenes to boronic acid pinacol esters via nickel catalysis is described. In contrast to other borylation protocols of inert C-O bonds, the method is competent in activating the carbon-oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Sequential cross-coupling reactions were achieved by leveraging the orthogonal reactivity of silyloxyarenes, which could then be functionalized subsequently.
Pein, Wesley L.,Wiensch, Eric M.,Montgomery, John
supporting information

(2021/06/28)

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation
Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.
K?nig, Burkhard,Wang, Hua,Wang, Shun
supporting information
p. 1653 - 1665
(2021/06/17)

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation
Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.
Geng, Shasha,Zhang, Juan,Chen, Shuo,Liu, Zhengli,Zeng, Xiaoqin,He, Yun,Feng, Zhang
supporting information
p. 5582 - 5588
(2020/07/08)

Organic compound with high mobility, and application thereof
The invention relates to an organic compound with high mobility, and application thereof. The organic compound provided by the invention takes a benzene ring connected with a five-membered parallel ring structure as a core, and has good thermal stability, high glass transition temperature and appropriate HOMO energy level. A device adopting the organic compound provided by the invention can effectively improve the photoelectric property of an OLED device and prolong the service life of the OLED device through structural optimization.
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Paragraph 0063-0064; 0065; 0068

(2020/09/23)

Iron-Catalyzed Borylation of Aryl Ethers via Cleavage of C-O Bonds
Herein, we report the iron-catalyzed borylation of aryl ethers and aryl amines via cleavage of C-O and C-N bonds. This protocol does not require the use of Grignard reagents and displays a broad substrate scope, which allows the late-stage borylation. It also provides facile access to multisubstituted arenes through C-H functionalization using 2-pyridyloxy as the directing group.
Zeng, Xiaoqin,Zhang, Yuxuan,Liu, Zhengli,Geng, Shasha,He, Yun,Feng, Zhang
p. 2950 - 2955
(2020/04/15)

Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides
This Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine nickel(aryl)(fluoride) intermediate. These investigations revealed that diboron reagents undergo transmetalation with this Ni(aryl)(fluoride) intermediate at rates significantly faster than their aryl boronate ester congeners. Furthermore, the reactivity of both boron reagents toward transmetalation is enhanced with increasing electrophilicity of the boron center. These mechanistic insights were leveraged to develop a catalytic decarbonylative borylation of acid fluorides that proved applicable to a variety of (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can be generated in situ directly from carboxylic acids. Furthermore, the mechanistic studies directed the identification of various air-stable Ni pre-catalysts for this transformation.
Malapit, Christian A.,Bour, James R.,Laursen, Simon R.,Sanford, Melanie S.
supporting information
p. 17322 - 17330
(2019/11/03)

Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles
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.
Ling, Liang,He, Yuan,Zhang, Xue,Luo, Meiming,Zeng, Xiaoming
supporting information
p. 6554 - 6558
(2019/04/17)

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions
Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.
Dai, Peng-Fei,Ning, Xiao-Shan,Wang, Hua,Cui, Xian-Chao,Liu, Jie,Qu, Jian-Ping,Kang, Yan-Biao
supporting information
p. 5392 - 5395
(2019/03/29)

Copper-catalysed borylation of aryl chlorides
We report herein the first Cu-catalysed borylation of a wide range of aryl chlorides with different electronic and steric properties using a readily prepared NHC-stabilised Cu catalyst and KOtBu as the base with B2pin2 (pin = pinacolato) as the boron reagent. The aryl chlorides are converted into their corresponding arylboronic esters in good yields. The new procedure shows broad functional group tolerance, and B2neop2 (neop = neopentyl glycolato) can also be applied as the boron reagent.
Kuehn, Laura,Huang, Mingming,Radius, Udo,Marder, Todd B.
supporting information
p. 6601 - 6606
(2019/07/16)

Nickel-catalysed decarbonylative borylation of aroyl fluorides
The first Ni(cod)2/PPh3 catalyst system has been established for decarbonylative borylation of aroyl fluorides with bis(pinacolato)diboron. A wide range of functional groups in the substrates were well tolerated. The ease of access of the starting aroyl fluorides indicates that these results might become an alternative to the existing decarbonylation events.
Wang, Zhenhua,Wang, Xiu,Nishihara, Yasushi
supporting information
p. 13969 - 13972
(2019/01/03)

Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation
Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C?O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.
Liu, Chengwei,Ji, Chong-Lei,Hong, Xin,Szostak, Michal
supporting information
p. 16721 - 16726
(2018/11/30)

Cobalt-Catalyzed C-F Bond Borylation of Aryl Fluorides
A mild and practical cobalt-catalyzed defluoroborylation of fluoroarenes is presented for the first time. The method permits straightforward functionalization of fluoroarenes, with high selectivity for borylation of C-F over C-H bonds, and a tolerance for aerobic conditions. Furthermore, two-step 18F-fluorination was achieved for expanding the scope of 18F-positron emission tomography probes.
Lim, Soobin,Song, Dalnim,Jeon, Seungwon,Kim, Youngsuk,Kim, Hyunseok,Lee, Sanghee,Cho, Hyungdo,Lee, Byung Chul,Kim, Sang Eun,Kim, Kimoon,Lee, Eunsung
supporting information
p. 7249 - 7252
(2018/11/23)

LiHMDS-Promoted Palladium or Iron-Catalyzed ipso-Defluoroborylation of Aryl Fluorides
A novel and efficient method for the synthesis of arylboronic acid pinacol esters via a palladium- or iron-catalyzed cross-coupling reaction of aryl fluorides with bis(pinacolato)diboron (B2pin2) in the presence of LiHMDS was developed. The Pd-catalyzed defluoroborylation of fluoroarenes is compatible with a variety of functional groups such as primary and secondary amine, ketone, trifluoromethyl, alkoxy, and boryl. Remarkably, no external ligand is required for enhanced conversion efficiency.
Zhao, Xianghu,Wu, Mingsheng,Liu, Yisen,Cao, Song
supporting information
p. 5564 - 5568
(2018/09/12)

ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY APPARATUS
The present invention relates to an organic optoelectronic device and a display apparatus comprising same, the organic optoelectronic device comprising: an anode and a cathode facing each other; a light-emitting layer located between the anode and cathode; a hole transport layer located between the anode and light-emitting layer; an auxiliary hole transport layer located between the hole transport layer and light-emitting layer; an electron transport layer located between the cathode and light-emitting layer; and an auxiliary electron transport layer between the electron transport layer and light-emitting layer, wherein the auxiliary electron transport layer comprises at least one type of a first compound expressed by a particular Chemical Formula, and the auxiliary hole transport layer comprises at least one type of a second compound expressed by a particular Chemical Formula.
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Paragraph 0204-0207

(2017/12/15)

The Rolling-Up of Oligophenylenes to Nanographenes by a HF-Zipping Approach
Intramolecular aryl–aryl coupling is the key transformation in the rational synthesis of nanographenes and nanoribbons. In this respect the C?F bond activation was shown to be a versatile alternative enabling the synthesis of several unique carbon-based nanostructures. Herein we describe an unprecedentedly challenging transformation showing that the C?F bond activation by aluminum oxide allows highly effective domino-like C?C bond formation. Despite the flexible nature of oligophenylene-based precursors efficient regioselective zipping to the target nanostructures was achieved. We show that fluorine positions in the precursor structure unambiguously dictate the “running of the zipping-program” which results in rolling-up of linear oligophenylene chains around phenyl moieties yielding target nanographenes. The high efficiency of zipping makes this approach attractive for the synthesis of unsubstituted nanographenes which are difficult to obtain in pure form by other methods.
Steiner, Ann-Kristin,Amsharov, Konstantin Y.
supporting information
p. 14732 - 14736
(2017/10/23)

Iron-Catalyzed Borylation of Aryl Chlorides in the Presence of Potassium t-Butoxide
A catalytic amount of an inorganic iron salt such as Fe(acac)3 catalyzes borylation of various aryl and heteroaryl chlorides with bis(pinacolato)diboron, where the presence of potassium t-butoxide is crucially important. The alkoxide is considered to produce in situ an electron-rich iron alkoxide complex as the active species. The reaction requires only an iron salt and potassium t-butoxide as promoters and is easily scalable. The arylboron compound prepared by this reaction can be further coupled in situ with an aryl halide under the Suzuki-Miyaura conditions.
Yoshida, Takumi,Ilies, Laurean,Nakamura, Eiichi
p. 3199 - 3203
(2017/06/09)

Azaindoles as Zinc-Binding Small-Molecule Inhibitors of the JAMM Protease CSN5
CSN5 is the zinc metalloprotease subunit of the COP9 signalosome (CSN), which is an important regulator of cullin-RING E3 ubiquitin ligases (CRLs). CSN5 is responsible for the cleavage of NEDD8 from CRLs, and blocking deconjugation of NEDD8 traps the CRLs in a hyperactive state, thereby leading to auto-ubiquitination and ultimately degradation of the substrate recognition subunits. Herein, we describe the discovery of azaindoles as a new class of CSN5 inhibitors, which interact with the active-site zinc ion of CSN5 through an unprecedented binding mode. The best compounds inhibited CSN5 with nanomolar potency, led to degradation of the substrate recognition subunit Skp2 in cells, and reduced the viability of HCT116 cells.
Altmann, Eva,Erbel, Paul,Renatus, Martin,Schaefer, Michael,Schlierf, Anita,Druet, Adelaide,Kieffer, Laurence,Sorge, Mickael,Pfister, Keith,Hassiepen, Ulrich,Jones, Matthew,Ruedisser, Simon,Ostermeier, Daniela,Martoglio, Bruno,Jefferson, Anne B.,Quancard, Jean
supporting information
p. 1294 - 1297
(2017/01/24)

Rhodium-Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids
Transformation of aromatic thioesters into arylboronic esters was achieved efficiently using a rhodium catalyst. The broad functional-group tolerance and mild conditions of the method have allowed for the two-step decarboxylative borylation of a wide range of aromatic carboxylic acids, including commercially available drugs.
Ochiai, Hidenori,Uetake, Yuta,Niwa, Takashi,Hosoya, Takamitsu
p. 2482 - 2486
(2017/02/23)

Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons
A catalytic Miyaura-type ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C-S bonds into C-B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation was observed in the reaction of diphenyl sulfide.
Bhanuchandra,Baralle, Alexandre,Otsuka, Shinya,Nogi, Keisuke,Yorimitsu, Hideki,Osuka, Atsuhiro
p. 2966 - 2969
(2016/07/06)

Rhodium-Catalyzed ipso-Borylation of Alkylthioarenes via C-S Bond Cleavage
Rhodium-catalyzed transformation of alkyl aryl sulfides into arylboronic acid pinacol esters via C-S bond cleavage is reported. In combination with transition-metal-catalyzed sulfanyl group-guided regioselective C-H borylation reactions of alkylthioarenes, this method allows the synthesis of a diverse range of multisubstituted arenes.
Uetake, Yuta,Niwa, Takashi,Hosoya, Takamitsu
p. 2758 - 2761
(2016/06/15)

Preparation method of high purity 2-bromotriphenylene
The invention discloses a preparation method of high purity 2-bromotriphenylene. The preparation method comprises the following steps: step one, obtaining a first intermediate, second intermediate-(biphenyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-boron dioxide; step two, drying the first intermediate, second intermediate-(biphenyl-2-yl)-4,4,5,5-tetramethyl-1,3,2-boron dioxide to obtain second intermediate-(4-bromophenyl)-1,1'-bibenzene; step three, adding the second intermediate-(4-bromophenyl)-1,1'-bibenzene, nitromethane, and iron trichloride into a container, heating to carry out reactions for three hours, cooling, adding water, and layering; condensing the organic phase until no water is left, adding ethanol, carrying out reflux, cooling to the room temperature, filtering, and drying to obtain the high purity 2-bromotriphenylene. The provided preparation method has the advantages of economy, simpleness, convenience, mild reaction conditions, good operation environment, and high yield.
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Paragraph 0016

(2017/03/14)

Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates
A new and efficient nickel-catalyzed decarbonylative borylation reaction of carboxylic acid esters with bis(pinacolato)-diboron has been developed. This transformation allows access to structurally diverse aryl as well as alkenyl and alkyl boronate esters with high reactivity, broad substrate scope, and excellent functional-group tolerance. Further experiments show that this protocol can be carried out on a gram scale and applied to orthogonal synthetic strategies.
Guo, Lin,Rueping, Magnus
supporting information
p. 16787 - 16790
(2016/11/17)

Zinc-Catalyzed Dual C-X and C-H Borylation of Aryl Halides
A zinc-catalyzed combined C-X and C-H borylation of aryl halides using B2pin2 (pin=OCMe2CMe2O) to produce the corresponding 1,2-diborylarenes under mild conditions was developed. Catalytic C-H bond activation occurs ortho to the halide groups if such a site is available or meta to the halide if the ortho position is already substituted. This method thus represents a novel use of a groupXII catalyst for C-H borylation. This transformation does not proceed via a free aryne intermediate, but a radical process seems to be involved. Two B or not two B: A novel catalytic system based on a ZnII-dtbpy precursor was developed for the preparation of 1,2-diborylarenes. This method represents a new type of catalytic process for diborylation of aryl halides via both C-X and C-H activation.
Bose, Shubhankar Kumar,Deissenberger, Andrea,Eichhorn, Antonius,Steel, Patrick G.,Lin, Zhenyang,Marder, Todd B.
supporting information
p. 11843 - 11847
(2015/10/05)

Preparation and reactions of 4-iodobutyl pinacolborate. Synthesis of substituted alkyl and aryl pinacolboronates via 4-iodobutyl pinacolborate utilizing tetrahydrofuran as the leaving group
Iodine reacts with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin), under ambient reaction conditions in THF, to form the iodoalkylborate species 2-(4-iodobutoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4-IboxBpin). Apparently, one-half equivalent of I2 reacts with HBpin to form IBpin in pentanes, which in turn cleaves THF to form the 4-IboxBpin. Alkyl and aryl Grignard reagents, prepared under Barbier conditions, then react with 4-IboxBpin to form the corresponding alkyl and aryl pinacolboronates while reforming and liberating THF as the leaving group.
Murphy, Chris L.,Hall, Aaron,Roberts, Emily J.,Ryan, Matthew D.,Clary, Jacob W.,Singaram, Bakthan
p. 3032 - 3033
(2015/02/19)

Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes for Diverse C-F Bond Functionalizations
Ni/Cu-catalyzed transformation of fluoroarenes to arylboronic acid pinacol esters via C-F bond cleavage has been achieved. Further versatile derivatization of an arylboronic ester has allowed for the facile two-step conversion of a fluoroarene to diverse functionalized arenes, demonstrating the synthetic utility of the method.
Niwa, Takashi,Ochiai, Hidenori,Watanabe, Yasuyoshi,Hosoya, Takamitsu
supporting information
p. 14313 - 14318
(2015/11/27)

Rhodium-catalyzed borylation of aryl 2-pyridyl ethers through cleavage of the carbon-oxygen bond: Borylative removal of the directing group
The rhodium-catalyzed reaction of aryl 2-pyridyl ethers with a diboron reagent results in the formation of arylboronic acid derivatives via activation of the C(aryl)-O bonds. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp2 nitrogen atom at the 2-position of the substrate and the use of a boron-based reagent were crucial for the activation of the relatively inert C(aryl)-O bond of aryl 2-pyridyl ethers.
Kinuta, Hirotaka,Tobisu, Mamoru,Chatani, Naoto
p. 1593 - 1600
(2015/03/05)

SYNTHESIS OF BORONIC ESTERS AND BORONIC ACIDS USING GRIGNARD REAGENTS
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.
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Paragraph 0075; 0079

(2013/03/26)

Synthesis and characterization of ortho-twisted asymmetric anthracene derivatives for blue organic light emitting diodes (OLEDs)
New ortho-twisted asymmetric anthracene derivatives have been synthesized and characterized. The anthracene derivatives show good thermal stability with high glass transition temperatures and a pure blue emission with a narrow full width at half maximum in a film state (λmax = 454 nm with 71 nm for 2-(2-methylnaphtathalene-1-yl)-9,10-di(naphthalene-2-yl)anthracene and λmax = 445 nm with 60 nm for 2-(biphenyl-2-yl)-9,10- di(naphthalene-2-yl)anthracene). A multi-layered device using 2-(2-methylnaphtathalene-1-yl)-9,10-di(naphthalene-2-yl)anthracene as an emitting material exhibits a maximum quantum efficiency of 3.61% (power efficiency of 2.15 lm/W, current efficiency of 3.55 cd/A) and blue Commission Internationale de l'Eclairage chromaticity coordinates (x = 0.15, y = 0.13). A fabricated device using 2-(biphenyl-2-yl)-9,10-di(naphthalene-2-yl)anthracene as an emitting material exhibits a maximum quantum efficiency of 3.7% (power efficiency of 2.11 lm/W, current efficiency of 3.55 cd/A) and a blue Commission Internationale de l'Eclairage chromaticity coordinates (x = 0.15, y = 0.12).
Shin, Min-Gi,Kim, Seul Ong,Park, Hyun Tae,Park, Sung Jin,Yu, Han Sung,Kim, Yun-Hi,Kwon, Soon-Ki
p. 1075 - 1082
(2012/03/27)

Hydride as a leaving group in the reaction of pinacolborane with halides under ambient Grignard and Barbier conditions. One-pot synthesis of alkyl, aryl, heteroaryl, vinyl, and allyl pinacolboronic esters
Grignard reagents (aliphatic, aromatic, heteroaromatic, vinyl, or allylic) react with 1 equiv of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane, PinBH) at ambient temperature in tetrahydrofuran (THF) to afford the corresponding pinacolboronates. The initially formed dialkoxy alkylborohydride intermediate quickly eliminates hydridomagnesium bromide (HMgBr) and affords the product boronic ester in very good yield. Hydridomagnesium bromide (HMgBr) in turn disproportionates to a 1:1 mixture of magnesium hydride (MgH2) and magnesium bromide (MgBr2) on addition of pentane to the reaction mixture. DFT calculations (Gaussian09) at the B3LYP/6-31G(d) level of theory show that disproportionation of HMgBr to MgH2 and MgBr2 is viable in the coordinating ethereal solvents. This reaction also can be carried out under Barbier conditions, where the neat PinBH is added to the flask prior to the in situ formation of Grignard reagent from the corresponding organic halide and magnesium metal. Pinacolboronic ester synthesis under Barbier conditions does not give Wurtz coupling side products from reactive halides, such as benzylic and allylic halides. The reaction between PinBH and various Grignard reagents is an efficient, mild, and general method for the synthesis of pinacolboronates.
Clary, Jacob W.,Rettenmaier, Terry J.,Snelling, Rachel,Bryks, Whitney,Banwell, Jesse,Wipke, W. Todd,Singaram, Bakthan
experimental part
p. 9602 - 9610
(2012/01/03)

Palladium-catalyzed borylation of sterically demanding aryl halides with a silica-supported compact phosphane ligand
Immobile but active: A silica-supported "compact" phosphane, Silica-SMAP, can be used in the Pd-catalyzed borylation of aryl chlorides or bromides with bis(pinacolato)diboron (see scheme). The Silica-SMAP/Pd system significantly expands the substrate scope of the borylation toward sterically and electronically challenging aryl halides.
Kawamorita, Soichiro,Ohmiya, Hirohisa,Iwai, Tomohiro,Sawamura, Masaya
supporting information; experimental part
p. 8363 - 8366
(2011/10/09)

Palladium-catalyzed hydrometalation and bismetalation of biphenylene
2-Silyl- and 2-borylbiphenyls have been synthesized by the palladium-catalyzed reaction of biphenylene with hydrosilanes and a hydroborane, respectively, via the cleavage of the four-membered ring of biphenylene. Under similar conditions, the C-C bond of
Matsuda, Takanori,Kirikae, Haruki
p. 3923 - 3925
(2011/10/03)

LUMINESCENT COMPOUNDS AND ELECTROLUMINESCENT DEVICE USING THE SAME
The present invention relates to organic electroluminescent compounds and organic electroluminescent devices employing the same. More specifically, the invention relates to organic electroluminescent compounds containing an anthracenyl group or an aryl group having an anthracenyl substituent m the aryl ring of fluorene or indenofluorene, as a blue electroluminescent material in an organic electroluminescent layer. The electroluminescent compounds according to the invention exhibit high luminous efficiency and excellent life property, so that an OLED device having very good operation lifetime can be prepared therefrom.
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(2011/04/14)

Ambient-temperature cobalt-catalyzed cycloaddition strategies to aromatic boronic esters
Figure presented The room-temperature cobalt-catalyzed [4 + 2] cycloaddition of alkynylboronates and 1,3-dienes provides a convenient and general method for the synthesis of benzene-based aromatic boronic esters. Two complementary aromatization strategies involving in situ elimination and DDQ oxidation were explored, with the latter finding more generality. Finally, the potential of this technique to generate highly functionalized biaryls has been demonstrated via the synthesis of chiral (racemic) DMAP catalysts.
Auvinet, Anne-Laure,Harrity, Joseph P. A.,Hilt, Gerhard
supporting information; experimental part
p. 3893 - 3896
(2010/08/06)

Platinum-catalysed diborylation of arynes: Synthesis and reaction of 1,2-diborylarenes
Arynes are found to be facilely inserted into bis(pinacolato)diboron by using a platinum-isocyanide catalyst, affording diverse 1,2-diborylarenes, which can be converted into o-terphenyls via Suzuki-Miyaura coupling reaction.
Yoshida, Hiroto,Okada, Kengo,Kawashima, Shota,Tanino, Kenji,Ohshita, Joji
supporting information; experimental part
p. 1763 - 1765
(2010/07/04)

An efficient catalyst system for palladium-catalyzed borylation of aryl halides with pinacolborane
The combination of Pd(dba)2 and bis(2-di-tert-butyl- phosphinophenyl)ether has proven to be efficient for the cross-coupling of pinacolborane with aryl bromides and chlorides. The substrate scope is broad and the present system enables the synthesis of ortho-, meta-, and para-substituted electron-rich and -deficient arylboronates. Georg Thieme Verlag Stuttgart.
Murata, Miki,Sambommatsu, Tomoko,Watanabe, Shinji,Masuda, Yuzuru
p. 1867 - 1870
(2008/02/08)