- Selective synthesis, structure and oxidation properties of isomeric 1,4-dithiins fused to two benzo[b]thiophenes
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Two novel isomers of 1,4-dithiins fused to two benzo[b]thiophenes on both sides were obtained by selective synthetic methods via the corresponding sulfides. The crystal structures of two dithiins were determined by X-ray crystallographic analyses. Examination of oxidation properties of the dithiins showed interesting results by CV measurement. The ESR spectra of chemically oxidized dithiins indicated formation of stable radical cations.
- Yamamoto, Tatsuya,Ogawa, Satoshi,Sato, Ryu
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Read Online
- A room-Temperature phosphorescent polymer film containing a molecular web based on one-dimensional chiral stacking of a simple luminophore
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We propose a new approach for a totally organic, room-Temperature phosphorescent system with a lifetime on the order of milliseconds, which is achieved by promotion of the one-dimensional chiral stacking of a simple, small fluorophore in a solution state. The versatility of this system is highlighted by its good applicability to the fabrication of a phosphorescent polymer film. This paper demonstrates the first example of a room-Temperature phosphorescent polymer film prepared with our methodology.
- Yoshida, Kyohei,Kuwahara, Yutaka,Miyamoto, Koji,Nakashima, Seiya,Jintoku, Hirokuni,Takafuji, Makoto,Ihara, Hirotaka
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Read Online
- Syntheses and properties of nine-ring-fused linear thienoacenes
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π-Extended nine-ring-fused linear thienoacenes 1a-c with internal thieno[3,2-b;4,5-b′]dithiophene substructures were synthesized. Their optical and electrochemical properties were investigated. Thin-film transistor characteristics showed all compounds displayed high device reproducibility and nearly no dependence on substrate temperatures. The highest performance was observed for 1c-based devices with mobility up to 1.0 cm2/Vs and current on/off ratio of 107, whereas the maximum mobility was 0.5 cm2/Vs for 1b and 0.011 cm2/Vs for 1a.
- Xiong, Yu,Qiao, Xiaolan,Wu, Hongzhuo,Huang, Qiuliu,Wu, Qinghe,Li, Jie,Gao, Xike,Li, Hongxiang
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Read Online
- Structure-property relationships of benzo[2,1-b:3,4-b']bis[1]benzothiophenes for organic field effect transistors
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A series of novel benzo[2,1-b:3,4-b']bis[1]-benzothiophene (BBBT) derivatives with different side-chains were synthesized and characterized. And their mobility properties were evaluated based on their active layers in OFETs devices. By means of simple thermal annealing, the devices based on BBBT-4 and BBBT-6 exhibited typical p-type FETs behavior with average hole mobilities of 0.28 and 0.124 cm2 V?1 s?1, respectively. Furthermore, the structure-property relationships of these semiconductors were also investigated by XRD and AFM.
- Zhang, Kai,Zhang, Ji,Huang, Lanqi,Zhang, Xiaoqin,Yu, Gui,Wong, Man Shing
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Read Online
- Benzothieno [3, 2-b] benzothiophene-like hole transport material and preparation method and application thereof
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The invention discloses a benzothieno [3, 2-b] benzothiophene-like hole transport material as well as a preparation method and application thereof. According to the invention, a benzo five-membered ring [3, 2-b] benzo five-membered ring (BXBY)-based hole
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Paragraph 0061-0064
(2021/06/26)
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- Thermally activated delayed fluorescent deep blue light material and preparation method thereof with organic electroluminescent device
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The present invention discloses a thermal activation delayed fluorescent deep blue light material and preparation method thereof and an organic electroluminescent device, the thermal activation delayed fluorescent deep blue light material having the follo
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Paragraph 0091-0095
(2022/01/08)
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- Flexible on-site halogenation paired with hydrogenation using halide electrolysis
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Direct electrochemical halogenation has appeared as an appealing approach in synthesizing organic halides in which inexpensive inorganic halide sources are employed and electrical power is the sole driving force. However, the intrinsic characteristics of direct electrochemical halogenation limit its reaction scope. Herein, we report an on-site halogenation strategy utilizing halogen gas produced from halide electrolysis while the halogenation reaction takes place in a reactor spatially isolated from the electrochemical cell. Such a flexible approach is able to successfully halogenate substrates bearing oxidatively labile functionalities, which are challenging for direct electrochemical halogenation. In addition, low-polar organic solvents, redox-active metal catalysts, and variable temperature conditions, inconvenient for direct electrochemical reactions, could be readily employed for our on-site halogenation. Hence, a wide range of substrates including arenes, heteroarenes, alkenes, alkynes, and ketones all exhibit excellent halogenation yields. Moreover, the simultaneously generated H2at the cathode during halide electrolysis can also be utilized for on-site hydrogenation. Such a strategy of paired halogenation/hydrogenation maximizes the atom economy and energy efficiency of halide electrolysis. Taking advantage of the on-site production of halogen and H2gases using portable halide electrolysis but not being suffered from electrolyte separation and restricted reaction conditions, our approach of flexible halogenation coupled with hydrogenation enables green and scalable synthesis of organic halides and value-added products.
- Shang, Xiao,Liu, Xuan,Sun, Yujie
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supporting information
p. 2037 - 2043
(2021/03/26)
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- Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**
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A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.
- Christmann, Mathias,He, Guoli,List, Benjamin
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supporting information
p. 13591 - 13596
(2021/05/07)
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- Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons
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Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.
- Chen, Yayun,He, Jiajia,Jiang, Chunhui,Ren, Xiaoyu,Su, Zhishan,Wang, Tianli,Xiao, Kai,Zhang, Hongkui,Zhuang, Cheng
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supporting information
p. 19860 - 19870
(2021/08/06)
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- Catalytic Asymmetric Dearomative 1,3-Dipolar Cycloaddition of 2-Nitrobenzothiophenes and Isatin-Derived Azomethine Ylides
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An enantioselective dearomative 1,3-dipolar cycloaddition of 2-nitrobenzothiophenes and isatin-derived azomethine ylides with a bifunctional hydrogen-bonding thiourea catalyst was established, giving polyheterocyclic compounds in excellent results (up to 99% yield, >20:1 dr for all cases and up to 99% ee). The enantioselectivity could be reversed by the bifunctional hydrogen-bonding squaramide catalyst containing the same chiral source as in the thiourea catalyst. DFT calculations revealed the origin of the observed stereochemistry and the reversal of enantioselectivity.
- Zhao, Jian-Qiang,Zhou, Shun,Yang, Lei,Du, Hong-Yan,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng
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supporting information
p. 8600 - 8605
(2021/11/13)
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- Bis(diphenylamino)-benzo[4,5]thieno[3,2-b]benzofuran as hole transport material for highly efficient RGB organic light-emitting diodes with low efficiency roll-off and long lifetime
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In this work, a novel hole transport material (HTM) based on benzo[4,5]thieno[3,2-b]benzofuran (BTBF) core with diphenylamine group, BTBF-DPA, was synthesized and systematically studied. BTBF-DPA showed high carrier mobility, good thermal stability and high triplet energy as 2.99 eV. Green phosphorescent organic light-emitting diodes (PhOLEDs) using BTBF-DPA were fabricated which displayed outstanding electroluminescent performance with a low turn-on voltage of 2.4 V, the maximum current efficiency (CE) of 123.6 cd A?1, power efficiency (PE) of 136.6 lm W?1, and external quantum efficiency (EQE) of 34.1%. Red PhOLEDs with BTBF-DPA also demonstrated a maximum PE of 40.1 lm W?1, and EQE of 24.9% with a low turn-on voltage of 2.3 V. Besides, blue fluorescence OLEDs presented a maximum PE of 4.9 lm W?1, EQE of 5.2% and small efficiency roll-off of 11.5% at 10000 cd m?2. RGB-OLEDs with BTBF-DPA outperformed the reference devices based on NPB as HTM that has been widely utilized. What's more, life-time of RGB OLEDs were T99 = 70 h at 10000 cd m?2, T70 = 60 h at 10000 cd m?2, T80 = 125 h at 5000 cd m?2, respectively. These results imply that BTBF-DPA is a promising HTM for OLEDs.
- Ali, Muhammad Umair,Fang, Daqi,He, Yaowu,Meng, Hong,Miao, Jingsheng,Shi, Ming,Sun, Yue,Wang, Tao,Wang, Yunrui,Zhang, Tian
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- POLYCYCLIC AROMATIC DERIVATIVE COMPOUNDS AND ORGANIC LIGHT-EMITTING ELEMENTS USING THE SAME
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PROBLEM TO BE SOLVED: To provide: organic light-emitting compounds used in organic layers of organic light-emitting elements and capable of realizing efficient and long-lasting organic light-emitting elements; and organic light-emitting elements comprising the same. SOLUTION: An organic light-emitting compound is such that Q1 to Q3 are linked by linkers Y and X at specific positions, where Q1 to Q3 are identical to or different from each other and each independently a substituted or unsubstituted C6-50 aromatic hydrocarbon ring or a substituted or unsubstituted C2-50 heteroaromatic ring; each of the linkers Y is one selected from among N-R1, CR2R3, O, S, Se and SiR4R5; the multiple linkers Y are identical to or different from each other; and X is one selected from among B, P and P=O. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0138-0142
(2020/06/30)
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- POLYCYCLIC AROMATIC COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICES USING THE SAME
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Disclosed are polycyclic aromatic compounds that can be employed in various organic layers of organic electroluminescent devices. Also disclosed are organic electroluminescent devices including the polycyclic aromatic compounds. The organic electroluminescent devices are highly efficient and long lasting and have greatly improved luminous efficiency.
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Paragraph 0088-0089
(2020/06/29)
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- ORGANIC COMPOUND AND ORGANIC LIGHT EMITTING DIODE INCLUDING SAME
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Disclosed herein are an organic light emitting compound represented by [Chemical Formula 1] below and an organic light emitting diode comprising same. In [Chemical Formula 1], the substituents R1 to R5, R11 to R18, R21 to R22, and R31 to R40, the linkers L1 to L3, and m1 and m2 are as defined in the description:.
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Paragraph 0340-0343
(2020/12/31)
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- ORGANIC ELECTROLUMINESCENT DEVICE
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Disclosed is an organic electroluminescent device that employs a compound represented by Formula A-1 or A-2: and a compound represented by Formula B: The organic electroluminescent device has excellent luminescent properties such as high color purity and long lifetime.
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Paragraph 0093-0094
(2020/12/30)
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- Diels-Alder reaction of tetraarylcyclopentadienones with benzo[: B] thiophene S, S-dioxides: An unprecedented de-oxygenation vs. sulfur dioxide extrusion
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Diels-Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene dioxides in xylenes at reflux led to the formation of tetra aryl-substituted dibenzothiophene as well as penta aryl-substituted benzene analogues depending on the influence of aryl substituents present on cyclopentadienones. The intermediate dihydrodibenzothiophene-dioxides underwent aromatization either through de-oxygenation or extrusion of sulfur dioxide to furnish substituted dibenzothiophenes or benzenes. This journal is
- Manikandan, Palani,Karunakaran, Jayachandran,Varathan, Elumalai,Schreckenbach, Georg,Mohanakrishnan, Arasambattu K.
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supporting information
p. 15317 - 15320
(2020/12/23)
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- Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes
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The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives containing two identical heteroatoms, namely, oxygen OOC, nitrogen NNC, or sulfur SSC. Two of described pathways involve the photocyclization of the corresponding triene 2 as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin 14 and benzo[b]heteroole 15. Typical functionalizations of the 5,10-diheterotruxene core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives because the universal method suitable for obtaining molecules with any type of heteroatoms is not known so far.
- Górski, Krzysztof,Mech-Piskorz, Justyna,Le?niewska, Barbara,Pietraszkiewicz, Oksana,Pietraszkiewicz, Marek
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p. 4672 - 4681
(2020/05/01)
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- Electrocatalytic Deuteration of Halides with D2O as the Deuterium Source over a Copper Nanowire Arrays Cathode
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Precise deuterium incorporation with controllable deuterated sites is extremely desirable. Here, a facile and efficient electrocatalytic deuterodehalogenation of halides using D2O as the deuteration reagent and copper nanowire arrays (Cu NWAs) electrochemically formed in situ as the cathode was demonstrated. A cross-coupling of carbon and deuterium free radicals might be involved for this ipso-selective deuteration. This method exhibited excellent chemoselectivity and high compatibility with the easily reducible functional groups (C=C, C≡C, C=O, C=N, C≡N). The C?H to C?D transformations were achieved with high yields and deuterium ratios through a one-pot halogenation–deuterodehalogenation process. Efficient deuteration of less-active bromide substrates, specific deuterium incorporation into top-selling pharmaceuticals, and oxidant-free paired anodic synthesis of high-value chemicals with low energy input highlighted the potential practicality.
- Chong, Xiaodan,Han, Shuyan,Li, Mengyang,Liu, Cuibo,Zhang, Bin
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supporting information
p. 18527 - 18531
(2020/08/21)
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- Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations
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While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.
- Deckers, Kristina,Fricke, Christoph,Schoenebeck, Franziska
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supporting information
p. 18717 - 18722
(2020/08/25)
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- Bis[1]benzothieno[1,4]thiazines: Planarity, Enhanced Redox Activity and Luminescence by Thieno-Expansion of Phenothiazine
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Twofold Buchwald–Hartwig aminations selectively furnish three regioisomers of bis[1]benzothieno[1,4]thiazines; X-ray structure analyses and DFT calculations were corroborated for correlation of their electronic properties. All regioisomers outscore the pa
- Schneeweis, Arno P. W.,Hauer, Simone T.,Reiss, Guido J.,Müller, Thomas J. J.
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supporting information
p. 3582 - 3590
(2019/02/14)
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- NEW SUBSTITUTED BENZONAPHTHATHIOPHENE COMPOUNDS FOR ORGANIC ELECTRONICS
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The present invention provides compounds of formulae (1) (2) wherein R1and R2are C1-30alkyl, C2-3O-alkenyl, C2-30-alkynyl, C5-7-cycloalkyl, C6-14-aryl or 5 to 14 membered heteroaryl, wherein C1-30-alkyl, C2-3O-alkenyl and C2-3O-alkynyl can be substituted with one or more substituents selected from the group consisting of halogen, phenyl, O-C1-20-alkyl, O-C2-20-alkenyl and O- C2-2O-alkynyl, and wherein C5-7-cycloalkyl, C6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one or more substituents selected from the group consisting of halogen, C1-20alkyl, C2-2O-alkenyl, C2-2O-alkynyl, O-C1-20-alkyl, O-C2-2o-alkenyl and O-C2-2o-alkynyl, Ra, Rb, Rcand Rdare independently and at each occurrence selected from the group consisting of C1-30alkyl, C2-30-alkenyl, C2-30-alkynyl, C6-14-aryl and 5 to 14 membered heteroaryl, wherein C1-30-alkyl, C2-3o-alkenyl and C2-3o-alkynyl can be substituted with one or more substituents selected from the group consisting of halogen, phenyl, O-C1-20-alkyl, O-C2-20-alkenyl and O- C2-20-alkynyl, and wherein C5-7-cycloalkyl, C6-14-aryl and 5 to 14 membered heteroaryl can be substituted with one or more substituents selected from the group consisting of halogen, C1-20alkyl, C2-2o-alkenyl, C2-20-alkynyl, O-C1-20-alkyl, O-C2-20-alkenyl and O-C2-2o-alkynyl, n and o are independently 0, 1, 2, 3, 4 or 5, and m and p are independently 0, 1, 2 or 3, and to electronic device comprising the compounds of formulae 1 or 2.
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Page/Page column 13
(2019/05/10)
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- Synergy of Anodic Oxidation and Cathodic Reduction Leads to Electrochemical C—H Halogenation
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We herein uncovered an electrochemical C—H halogenation protocol that synergistically combines anodic oxidation and cathodic reduction for C—X bond formation. The reaction was demonstrated under exogenous-oxidant-free conditions. Moreover, this is the first example of activating CBr4, CHBr3, and CCl3Br under electrochemical conditions.
- Zhou, Zhilin,Yuan, Yong,Cao, Yangmin,Qiao, Jin,Yao, Anjin,Zhao, Jing,Zuo, Wanqing,Chen, Wenjie,Lei, Aiwen
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supporting information
p. 611 - 615
(2019/05/10)
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- Phosphine-catalyzed dearomative (3 + 2) annulation of 2-nitrobenzofurans and nitrobenzothiophenes with allenoates
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An efficient Ph2PMe-catalyzed dearomative (3 + 2) annulation of 2-nitrobenzofurans, 2-nitrobenzothiophenes, and 3-nitrobenzothiophenes with allenoates has been developed. With the developed protocol, a series of structurally important cyclopenta[b]benzofurans and cyclopenta[b]benzothiophenes were obtained in good to excellent yields (up to 98%) under mild conditions. In addition, preparative-scale experiments and transformations were conducted to exemplify the synthetic utility. The asymmetric version of this dearomative (3 + 2) annulation reaction was tentatively investigated by using chiral phosphine catalysts.
- Zhao, Jian-Qiang,Yang, Lei,You, Yong,Wang, Zhen-Hua,Xie, Ke-Xin,Zhang, Xiao-Mei,Xu, Xiao-Ying,Yuan, Wei-Cheng
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p. 5294 - 5304
(2019/06/07)
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- Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
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Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.
- Fredrich, Sebastian,Bonasera, Aurelio,Valderrey, Virginia,Hecht, Stefan
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supporting information
p. 6432 - 6440
(2018/05/31)
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- PPAR (peroxisome proliferator-activated receptor) agonist and application thereof to treatment of senile dementia and other diseases
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The invention relates to a compound, namely a gamma-subtype peroxisome proliferator-activated receptor (PPAR) agonist. In addition, the invention discloses a medicinal component and a preparation containing the compound and application of such the gamma-subtype PPAR agonist.
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Paragraph 0381; 0384-0386
(2018/07/30)
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- Cu/Fe/O=PPh3-catalyzed etherification for the synthesis of aryl 3-benzo[b]thienyl ethers
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Cu/Fe-cocatalyzed cross-coupling reactions between 3-bromobenzo[b]thiophene and hydroxyaryls are described herein. The combination of Cu and Fe catalysts is important for the progress of the reactions, and the use of triphenylphosphine oxide as a ligand suppresses the dehalogenation of 3-bromobenzo[b]thiophene, and promptly facilitates the reaction. The obtained aryl benzo[b]thienyl ethers can be converted to π-extended thienobenzofuran derivatives via Pd-catalyzed dehy-drogenative cyclizations.
- Mitsudo, Koichi,Asada, Takuya,Inada, Tomohiro,Kurimoto, Yuji,Mandai, Hiroki,Suga, Seiji
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supporting information
p. 1044 - 1047
(2018/08/24)
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- Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
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Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.
- Quibell, Jacob M.,Perry, Gregory J. P.,Cannas, Diego M.,Larrosa, Igor
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p. 3860 - 3865
(2018/04/26)
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- Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling to Form Highly Substituted 1,3-Dienes
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The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5′-bis(trifluoromethyl)-2,2′-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers.
- Olivares, Astrid M.,Weix, Daniel J.
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supporting information
p. 2446 - 2449
(2018/02/28)
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- Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans
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Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%–92%), diastereoselectivity (13/1 → >20/1 dr), and enantioselectivity (75%–95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.
- Cheng, Qiang,Zhang, Hui-Jun,Yue, Wen-Jun,You, Shu-Li
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supporting information
p. 428 - 436
(2017/09/22)
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- Heterocyclic compound and organic light-emitting device comprising the same
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Disclosed are a heterocyclic compound and an organic light-emitting device comprising the same. The heterocyclic compound is represented by chemical formula 1. The organic light-emitting device comprising the heterocyclic compound can have low driving voltage, high brightness, high efficiency, and long lifespan.COPYRIGHT KIPO 2016
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Paragraph 0592-0594
(2016/10/08)
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- One-Pot Trimetallic Relay Catalysis: A Unified Approach for the Synthesis of β-Carbolines and Other [c]-Fused Pyridines
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A divergent strategy is presented for the synthesis of 1,3-di- and 1,3,4-trisubstituted β-carbolines through an unprecedented one-pot triple-orthogonal-metal relay catalysis, and 1,3-disubstituted 4-hydroxy-β-carbolines through a one-pot bimetallic relay
- Dhiman, Seema,Mishra, Uttam K.,Ramasastry
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supporting information
p. 7737 - 7741
(2016/07/07)
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- ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING THE SAME
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The present invention relates to a novel organic compound and an organic electroluminescence device including the same. The compound including dihydrothienoquinoline core is applied as a material for an organic electroluminescence device, preferably as a host material of a light emitting layer, so that the organic electroluminescence device has the improved properties such as light emitting efficiency, driving voltage, and life.COPYRIGHT KIPO 2015
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Paragraph 0069-0072
(2016/11/14)
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- Synthesis and Characterization of a Two Stage, Nonlinear Photobase Generator
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Amine photobase generators (PBGs) are uncommon yet useful compounds. Rarer still are examples of PBGs that are active at visible wavelengths. We report the synthesis and characterization of new photolabile amine protecting groups that are active under visible light. The new chromophore, benzothiophene imino-phenylacetonitrile (BTIPA), was synthesized in four steps without use of chromatography and found to release any one of several amines upon exposure to 405 nm light. The chromophore was also demonstrated to be useful as a Merrifield synthesis protecting group. Experimental evidence suggests a sequential, two stage photolysis mechanism which leads to a nonlinear response to dose.
- Hayes, Colin O.,Bell, William K.,Cassidy, Benjamin R.,Willson, C. Grant
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p. 7530 - 7535
(2015/08/18)
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- ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING AND PRODUCTION THEREOF
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In one embodiment, provided are a new class of diarylethene-containing photochromic compounds with the incorporation of silicon-or phosphorus-containing heterocycles into the "ethene" part of the diarylethene backbone that has been shown to be capable of displaying tunable, robust and thermally stable photochromic properties. Also provided are methods for synthesizing these compounds, as well as uses of these compounds as these compounds may be used as the photochromic layer in an optical recording material and other optical functioning devices.
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- INHIBITORS OF THE KYNURENINE PATHWAY
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The present application provides novel inhibitors of indoleamine 2,3-dioxygenase-1 and/or indoleamine 2,3-dioxygenase-2 and/or tryptophan 2,3-dioxygenase, metabolites thereof, and phannaceutically acceptable salts or prodrugs thereof. Also provided are methods for preparing these compounds. A therapeutically effective amount of one or more of the compounds of formula (I) is useful in treating diseases resulting from dysregulation of the kynurenine pathway. Compounds of formula (I) act by inhibiting the enzymatic activity or expression of indoleamine 2,3-dioxygenase-1 and/or indoleamine 2,3-dioxygenase-2 and/or tryptophan 2,3-dioxygenase.
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Page/Page column 186; 187
(2014/12/12)
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- NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles
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The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.
- Chelucci, Giorgio,Figus, Susanna
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p. 191 - 209
(2014/07/21)
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- Palladium-catalyzed intermolecular coupling of 2-silylaryl bromides with alkynes: Synthesis of benzosiloles and heteroarene-fused siloles by catalytic cleavage of the C(sp3)-Si bond
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Unusual split: A wide variety of benzosiloles and derivatives are obtained by the Pd-catalyzed intermolecular coupling of 2-silylaryl bromides and alkynes and the accompanying selective cleavage of the C(sp3)-Si bonds as a key step (see scheme). The product spectrum includes benzosiloles, benzothiophene-fused siloles, ladder-type π-conjugated benzosiloles, and thiophene-bridged 2,5-bisbenzosiloles.
- Liang, Yun,Geng, Weizhi,Wei, Junnian,Xi, Zhenfeng
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supporting information; experimental part
p. 1934 - 1937
(2012/03/26)
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- Synthesis of annulated oligothiophenes
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Reactions of 1,1-di(2-naphthyl)-2,2-dichloroethene and 1,1-di(2- benzothienyl)-2,2-dichloroethene with sulfur at 220-225 C resulted in hitherto unknown oligothiophenes. Tetrathio[6]helicene was synthesized from 1,1-di(3-benzothienyl)-2,2-dichloroethene. Preparative pathway to helicene involving intramolecular ring closure of dithiol derived from 1,1-di-(3-benzothienyl)-2,2-dichloroethene was developed as an alternative to high temperature synthesis.
- Nenajdenko,Balenkova,Chernichenko,Vshivenko
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p. 1456 - 1462
(2013/11/19)
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- Room-temperature hydrodehalogenation of halogenated heteropentalenes with one or two heteroatoms
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The pair NaBH4-TMEDA as a hydride source and catalytic PdCl 2(dppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes with one or two heteroatoms, while Pd(OAc)2/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.
- Chelucci, Giorgio,Baldino, Salvatore,Ruiu, Andrea
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p. 9921 - 9925,5
(2012/12/12)
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- Novel semiconductors based on functionalized benzo[ d, d′]thieno[3,2- b;4,5- b′]dithiophenes and the effects of thin film growth conditions on organic field effect transistor performance
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A series of benzo[d,d]thieno[3,2-b;4,5-b]dithiophene (BTDT) derivatives, end-functionalized with phenyl (P) and benzothiophenyl (BT), were synthesized and characterized. A facile, one-pot synthesis of BTDT was developed which enables the efficient realiza
- Youn, Jangdae,Chen, Ming-Chou,Liang, You-Jhih,Huang, Hui,Ortiz, Rocio Ponce,Kim, Choongik,Stern, Charlotte,Hu, Tarng-Shiang,Chen, Liang-Hsiang,Yan, Jing-Yi,Facchetti, Antonio,Marks, Tobin J.
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experimental part
p. 5031 - 5041
(2011/12/22)
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- Regioselective copper-catalyzed chlorination and bromination of arenes with O2 as the oxidant
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Electron-rich aromatic C-H bonds undergo regioselective chlorination and bromination in the presence of CuX2, LiX (X = Cl, Br) and molecular oxygen. Preliminary mechanistic insights suggest that the bromination and chlorination reactions proceed by different pathways.
- Yang, Lujuan,Lu, Zhan,Stahl, Shannon S.
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supporting information; experimental part
p. 6460 - 6462
(2010/03/04)
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- Synthesis and properties of the anti and syn isomers of dibenzothieno[b,d]pyrrole
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A novel type of anti and syn isomers of a pentacyclic compound consisting of two thiophene rings and one pyrrole ring were efficiently synthesized from benzo[b]thiophene, and the anti isomer exhibits better charge transport and OFET properties compared with the syn isomer and its N-hexyl substitution. The Royal Society of Chemistry.
- Qi, Ting,Guo, Yunlong,Liu, Yunqi,Xi, Hongxia,Zhang, Hengjun,Gao, Xike,Liu, Ying,Lu, Kun,Du, Chunyan,Yu, Giu,Zhu, Daoben
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supporting information; experimental part
p. 6227 - 6229
(2009/05/06)
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- Halocyclization of 2-alkynylthioanisoles by cupric halides: synthesis of 2-substituted 3-halobenzo[b]thiophenes
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Reaction of 2-alkynylthioanisoles 3 with 2 equiv of CuX2 (X=Br or Cl) in refluxing CH3CN for 2.5 h gave the 2-substituted 3-halobenzo[b]thiophenes 4 in good yields.
- Lu, Wen-Der,Wu, Ming-Jung
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p. 356 - 362
(2007/10/03)
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- A flexible approach to different families of bidentate P,P ligands as highly efficient ligands for asymmetric catalysis
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A novel and versatile approach has led to the synthesis of various classes of mono- and bidentate phospholane and phosphinite ligands based on a benzothiophene scaffold. The ligand functions in the bidentate ligands can be introduced independently and consecutively. A bis-phospolane ligand as well as its rhodium complex have been characterized by crystal-structure determinations. The bis-phospholane ligands were tested in the catalysed asymmetric homogeneous hydrogenation of dehydroamino acid derivatives, enamides and itaconates and gave ee values of up to 98.7 %. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Berens, Ulrich,Englert, Ulli,Geyser, Stefan,Runsink, Jan,Salzer, Albrecht
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p. 2100 - 2109
(2007/10/03)
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- An efficient phosphine-free palladium coupling for the synthesis of new 2-arylbenzo[b]thiophenes
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Straightforward and rapid access to 2-arylbenzo[b]thiophenes has been developed. It involved a catalytic coupling of 3-activated benzo[b]thiophenes with several aryl halides in the presence of a phosphine-free palladium system. In case of fragile functional groups such as aldehydes, a quaternary ammonium was used as an additive as with the other substrates, the coupling performed better and faster in the presence of a crown ether, the best one being DCH-18-C-6, with good yields and low reaction times. This method would provide a direct access to novel structures of biological interest.
- Dit Chabert, Jérémie Fournier,Joucla, Lionel,David, Emilie,Lemaire, Marc
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p. 3221 - 3230
(2007/10/03)
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- Piperidine derivatives as reuptake inhibitors
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The present invention provides compounds of formula (I) and a method of inhibiting the reuptake of serotonin and antagonizing the serotonin receptor which comprises administering to a subject in need of such treatment an effective amount of a compound of formula (I).
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Page column 53
(2010/02/09)
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- (Diacetoxyiodo)benzene-Lithium Bromide as a Convenient Electrophilic Br+ Source
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A mild and versatile procedure for the bromination of olefins and activated arenes by in situ generation of 'Br+' using (diacetoxyiodo)benzene and lithium bromide is presented. The reactions were carried out in open vessels at room temperature and were typically complete in 30 minutes. The brominated products were isolated by column chromatography, which also allowed for the isolation of the iodobenzene by-product for recycle.
- Braddock, D. Christopher,Cansell, Gemma,Hermitage, Stephen A.
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p. 461 - 464
(2007/10/03)
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- Synthesis of novel chiral thiophene-, benzothiophene- and benzofuran-oxazoline ligands and their use in the enantioselective Pd-catalyzed allylation
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Novel thiophene, benzothiophene and benzofuran-oxazoline ligands 6-11 containing a diphenylphosphino group at different positions of the heterocyclic skeleton have been prepared and used in the enantioselective allylation. The advantage of these new ligands is their easy accessibility and their high reactivity. The best results were obtained with ligand 9 to give the product 13 in 97.0% ee with 92% yield in 2 hours at 0°C.
- Tietze, Lutz F.,Lohmann, J. Klaas
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p. 2083 - 2085
(2007/10/03)
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- Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties
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Insulin resistance in the liver and peripheral tissues, together with a pancreatic cell defect, are the common causes of Type 2 diabetes. It is now appreciated that insulin resistance can result from a defect in the insulin receptor signaling system, at a site post binding of insulin to its receptor. Protein tyrosine phosphatases (PTPases) have been shown to be negative regulators of the insulin receptor. Inhibition of PTPases may be an effective method in the treatment of Type 2 diabetes. We have identified two novel series of benzofuran/benzothiophene biphenyl oxo-acetic acids and sulfonyl- salicylic acids as potent inhibitors of PTP1B with good oral antihyperglycemic activity. To assist in the design of these inhibitors, crystallographic studies have attempted to identify enzyme inhibitor interactions. Resolution of crystal complexes has suggested that the inhibitors bind to the enzyme active site and are held in place through hydrogen bonding and van der Waals interactions formed within two hydrophobic pockets. In the oxo-acetic acid series, hydrophobic substitutents at position-2 of the benzofuran/benzothiophene biphenyl framework interacted with Phe182 of the catalytic site and were very critical to the intrinsic activity of the molecule. The hydrophobic region of the catalytic-site pocket was exploited and taken advantage by hydrophobic substituents at either the α-carbon or the ortho aromatic positions of the oxo-acetic acid moiety. Similar ortho aromatic substitutions on the salicylic acid-type inhibitors had no effect, primarily due to the different orientation of these inhibitors in the catalytic site. The most active inhibitors of both series inhibited recombinant human PTP1B with phosphotyrosyl dodecapeptide TRDI(P)YETD(P)Y(P)YRK as the source of the substrate with IC50 values in the range of 20-50 nM. Compound 68 was one of the most active compounds in vivo, normalizing plasma glucose levels at the 25 mg/kg dose (po) and the 1 mg/kg dose (ip). Compound 68 was also selective against several other PTPases.
- Malamas, Michael S.,Sredy, Janet,Moxham, Christopher,Katz, Alan,Xu, Weixin,McDevitt, Robert,Adebayo, Folake O.,Sawicki, Diane R.,Seestaller, Laura,Sullivan, Donald,Taylor, Joseph R.
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p. 1293 - 1310
(2007/10/03)
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