- A new class of organic semiconductors for solution processed OTFTs: Synthesis and characterization of pyrrolo-perylene derivatives with different end groups
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New pyrrolo-perylene derivatives, a new class of organic semiconductor, were designed for solution processed organic thin film transistors (OTFTs). Newly designed 2-(naphthalen-2-yl)thiophene end capped pyrrolo-perylene, 3,10-bis(5-(naphthalen-2-yl)thiophen-2-yl)-1-(2-octyldodecyl)-1H-phenanthro[1, 10,9,8-cdefg]carbazole (NTPP), and bithiophene end capped pyrrolo-perylene, 3,10-bis([2,2′-bithiophen]-5-yl)-1-(2-octyldodecyl)-1H-phenanthro[1,10,9, 8-cdefg]carbazole (BTPP), were synthesized by Suzuki coupling and Stille coupling reaction, respectively. NTPP and BTPP showed good solubility in common organic solvents and were characterized by various spectroscopy. Solution processed OTFTs using BTPP exhibited high field-effect mobilities up to 0.11 cm2 V-1 s-1 with an on/off ratio of 1 × 104 and a very small threshold voltage of 0 V, while OTFTs using NTPP exhibited far lower performances. The high mobility of BTPP is attributed to three dimensional multi-layered crystalline structure based on the results of the two dimensional grazing incidence X-ray diffraction pattern analysis and theoretical calculation using Gaussian, together with morphological study.
- Park, Kwang Hun,Yun, Hui-Jun,Lu, Wanxiang,Chung, Dae Sung,Kwon, Soon-Ki,Kim, Yun-Hi
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- (Z)-3-chloro-3-(2-naphthyl)prop-2-enal in the synthesis of naphthyl-substituted thiophene and quinolines
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2-(2-Naphthyl)thiophene was synthesized by condensation of 3-chloro-3-(2-naphthyl)prop-2-enal with sulfanylacetic acid. A modified procedure was proposed for the synthesis of 2-(2-naphthyl)-and 2-(2-naphthyl)-6-nitroquinolines from 3-chloro-3-(2-naphthyl)prop-2-enal.
- Vashkevich,Potkin,Kozlov
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- Cross-coupling of aryl grignard reagents with aryl iodides and bromides through SRN1 pathway
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Game, SET, and match: Aryl Grignard reagents undergo coupling with aryl halides when toluene is used as a solvent in combination with a small amount of tetrahydrofuran (see scheme). The reaction proceeds through an SRN1 mechanism, and does not require any transition metal catalysts.
- Shirakawa, Eiji,Hayashi, Yumi,Itoh, Ken-Ichi,Watabe, Ryo,Uchiyama, Nanase,Konagaya, Wataru,Masui, Seiji,Hayashi, Tamio
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- Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings
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Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.
- Wang, Zhen-Yu,Ma, Biao,Xu, Hui,Wang, Xing,Zhang, Xu,Dai, Hui-Xiong
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p. 8291 - 8295
(2021/11/13)
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- Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry
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The Suzuki–Miyaura cross-coupling between polyfluorinated arylboron nucleophiles and aryl halides enables the efficient construction of polyfluorinated structural motifs frequently found in organic materials and catalysts. A key challenge associated with
- Takahashi, Rikuro,Seo, Tamae,Kubota, Koji,Ito, Hajime
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p. 14803 - 14810
(2021/12/09)
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- Cross-Electrophile C(sp2)?Si Coupling of Vinyl Chlorosilanes
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The cross-electrophile coupling has become a powerful tool for C?C bond formation, but its potential for forging the C?Si bond remains unexplored. Here we report a cross-electrophile Csp2-Si coupling reaction of vinyl/aryl electrophiles with vinyl chlorosilanes. This new protocol offers an approach for facile and precise synthesis of organosilanes with high molecular diversity and complexity from readily available materials. The reaction proceeds under mild and non-basic conditions, demonstrating a high step economy, broad substrate scope, wide functionality tolerance, and easy scalability. The synthetic utility of the method is shown by its efficient accessing of silicon bioisosteres, the design of new BCB-monomers, and studies on the Hiyama cross-coupling of vinylsilane products.
- Duan, Jicheng,Kang, Shaolin,Liu, Xue-Yuan,Qi, Liangliang,Shu, Xing-Zhong,Wang, Ke,Xu, Guang-Li
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p. 23083 - 23088
(2020/12/09)
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- Heterogeneous Nickel-Catalyzed Cross-Coupling between Aryl Chlorides and Alkyllithiums Using a Polystyrene-Cross-Linking Bisphosphine Ligand
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A polystyrene-cross-linking bisphosphine ligand PS-DPPBz was used for Ni-catalyzed cross-coupling with organolithiums. A bench-stable precatalyst [NiCl2(PS-DPPBz)] enabled efficient coupling reactions between aryl chlorides and alkyllithiums. The heterogeneous Ni system showed good reusability. (Figure presented.).
- Yamazaki, Yuki,Arima, Nozomi,Iwai, Tomohiro,Sawamura, Masaya
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p. 2250 - 2254
(2019/03/21)
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- Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents
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Cross-coupling of (hetero)arylthiols with arylzinc reagents via C-S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.
- Yang, Bo,Wang, Zhong-Xia
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supporting information
p. 6220 - 6223
(2017/11/24)
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- Mono- and dinuclear cyclopalladates as catalysts for Suzuki–Miyaura cross-coupling reactions in predominantly aqueous media
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Suzuki–Miyaura cross-coupling reactions of aryl halides with arylboronic acids were performed in predominantly aqueous media employing two mono- and two dinuclear cyclopalladated complexes as catalysts. These complexes are [Pd(HL)Cl] (I), [Pd(L)(PPh3)] (II), [Pd2(μ-dppb)(L)2] (III) and [Pd2(μ-dppf)(L)2] (IV); where H2L, dppb and dppf represent 4-methoxy-N′-(mesitylidene)benzohydrazide, 1,4-bis(diphenylphosphino)butane and 1,1′-bis(diphenylphosphino)ferrocene, respectively. The reactions were conducted using potassium carbonate as base in presence of tetrabutylammonium bromide (TBAB) at 70/90 °C in dimethylformamide–water (1:20) mixture. Among the four catalysts used, the dinuclear complex IV turned out to be the most effective and afforded moderate to excellent yields with broad substrate scope.
- Babu, G. Narendra,Pal, Samudranil
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p. 1000 - 1005
(2017/02/18)
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- Biarylalkyl Carboxylic Acid Derivatives as Novel Antischistosomal Agents
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Parasitic platyhelminths are responsible for serious infectious diseases, such as schistosomiasis, which affect humans as well as animals across vast regions of the world. The drug arsenal available for the treatment of these diseases is limited; for example, praziquantel is the only drug currently used to treat ≥240 million people each year infected with Schistosoma spp., and there is justified concern about the emergence of drug resistance. In this study, we screened biarylalkyl carboxylic acid derivatives for their antischistosomal activity against S. mansoni. These compounds showed significant influence on egg production, pairing stability, and vitality. Tegumental lesions or gut dilatation was also observed. Substitution of the terminal phenyl residue in the biaryl scaffold with a 3-hydroxy moiety and derivatization of the terminal carboxylic acid scaffold with carboxamides yielded compounds that displayed significant antischistosomal activity at concentrations as low as 10 μm with satisfying cytotoxicity values. The present study provides detailed insight into the structure–activity relationships of biarylalkyl carboxylic acid derivatives and thereby paves the way for a new drug-hit moiety for fighting schistosomiasis.
- M?der, Patrick,Blohm, Ariane S.,Quack, Thomas,Lange-Grünweller, Kerstin,Grünweller, Arnold,Hartmann, Roland K.,Grevelding, Christoph G.,Schlitzer, Martin
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supporting information
p. 1459 - 1468
(2016/07/16)
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- Palladacycles derived from arylphosphinamides for mild Suzuki-Miyaura cross-couplings
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We present a type of palladacyclic complexes derived from arylphosphinamides which can be used as efficient and versatile precatalysts for mild Suzuki-Miyaura cross-coupling. With the presence of 1.0 mol% of palladacycles, a wide variety of aryl bromides and boronic acids could be coupled very efficiently at ambient temperature and under air atmosphere without the need of external supporting ligands. Moreover, the mild conditions also allow for smooth coupling of electron-deficient, i.e., the less stable aryl triflates. In addition to the highly catalytic activity, the palladacyclic complexes can be very easily prepared through a two-step procedure from the readily affordable diphenyl-phosphinic chloride and exhibit excellent stability toward air and moisture. Due to these prominent properties, the new palladacycles would find practical use in Suzuki-Miyaura couplings.
- Wu, Guo-Jie,Han, Fu-She,Zhao, Yu-Long
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p. 69776 - 69781
(2015/09/01)
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- Alkenes as alkyne equivalents in radical cascades terminated by fragmentations: Overcoming stereoelectronic restrictions on ring expansions for the preparation of expanded polyaromatics
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Chemoselective interaction of aromatic enynes with Bu3Sn radicals can be harnessed for selective cascade transformations, yielding either Sn-substituted naphthalenes or Sn-indenes. Depending on the substitution at the alkene terminus, the initial regioselective 5-exo-trig cyclizations can be intercepted at the 5-exo stage via either hydrogen atom abstraction or C-S bond scission or allowed to proceed further to the formal 6-endo products via homoallylic ring expansion. Aromatization of the latter occurs via β-C-C bond scission, which is facilitated by 2c,3e through-bond interactions, a new stereoelectronic effect in radical chemistry. The combination of formal 6-endo-trig cyclization with stereoelectronically optimized fragmentation allows the use of alkenes as synthetic equivalents of alkynes and opens a convenient route to α-Sn-substituted naphthalenes, a unique launching platform for the preparation of extended polyaromatics.
- Mohamed, Rana K.,Mondal, Sayantan,Gold, Brian,Evoniuk, Christopher J.,Banerjee, Tanmay,Hanson, Kenneth,Alabugin, Igor V.
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supporting information
p. 6335 - 6349
(2015/06/02)
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- Organoaluminum-Mediated Direct Cross-Coupling Reactions
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We present a direct cross-coupling reaction between arylaluminum compounds (ArAlMe2·LiCl) and organic halides RX (R=aryl, alkenyl, alkynyl; X=I, Br, and Cl) without any external catalyst. The reaction takes place smoothly, simply upon heating, thereby enabling the efficient and chemo-/stereoselective formation of biaryl, alkene, and alkyne coupling products with broad functional group compatibility.
- Minami, Hiroki,Saito, Tatsuo,Wang, Chao,Uchiyama, Masanobu
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p. 4665 - 4668
(2015/04/14)
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- Palladium-Catalysed Direct Cross-Coupling of Organolithium Reagents with Aryl and Vinyl Triflates
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A palladium-catalysed cross-coupling of organolithium reagents with aryl and vinyl triflates is presented. The reaction proceeds at 50 or 70 C with short reaction times, and the corresponding products are obtained with moderate to high yields, with a variety of alkyl and (hetero)aryl lithium reagents.
- Vila, Carlos,Hornillos, Valentín,Giannerini, Massimo,Fa?anás-Mastral, Martín,Feringa, Ben L.
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supporting information
p. 13078 - 13083
(2016/02/19)
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- Single-electron-transfer-induced coupling of arylzinc reagents with aryl and alkenyl halides
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Arylzinc reagents, prepared from aryl halides/zinc powder or aryl Grignard reagents/zinc chloride, were found to undergo coupling with aryl and alkenyl halides without the aid of transition-metal catalysis to give biaryls and styrene derivatives, respectively. In this context, we have already reported the corresponding reaction using aryl Grignard reagents instead of arylzinc reagents. Compared with the Grignard cross-coupling, the present reaction features high functional-group tolerance, whereby electrophilic groups such as alkoxycarbonyl and cyano groups are compatible as substituents on both the arylzinc reagents and the aryl halides. Aryl halides receive a single electron and thereby become activated as the corresponding anion radicals, which react with arylzinc reagents, thus leading to the cross-coupling products. Arylzinc reagents were found to undergo coupling with aryl and alkenyl halides to give biaryl and styrene derivatives, respectively. The cross-coupling, which features high functional-group tolerance, proceeds through a single-electron-transfer mechanism and thus does not require the aid of transition-metal catalysis.
- Shirakawa, Eiji,Tamakuni, Fumiko,Kusano, Eugene,Uchiyama, Nanase,Konagaya, Wataru,Watabe, Ryo,Hayashi, Tamio
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supporting information
p. 521 - 525
(2014/01/23)
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- Direct C-C bond construction from arylzinc reagents and aryl halides without external catalysts
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Direct cross-coupling between an arylzinc reagent and an aryl halide was accomplished without any external catalyst, enabling efficient and selective formation of the corresponding biaryl compound with broad functional group compatibility. Direct cross-coupling between a diarylzinc compound and an aryl iodide was accomplished without using any external catalyst. The reaction is efficient and selective, enabling formation of the corresponding biaryl compounds with broad functional group compatibility. The reaction is proposed to proceed by a thermally initiated single electron transfer (SET) route. Copyright
- Minami, Hiroki,Wang, Xuan,Wang, Chao,Uchiyama, Masanobu
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supporting information
p. 7891 - 7894
(2014/01/06)
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- Catalytic direct cross-coupling of organolithium compounds with aryl chlorides
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Palladium-catalyzed direct cross-coupling of aryl chlorides with a wide range of (hetero)aryl lithium compounds is reported. The use of Pd-PEPPSI-IPent or Pd2(dba)3/XPhos as the catalyst allows for the preparation of biaryl and heterobiaryl compounds in high yields under mild conditions (room temperature to 40 C) with short reaction times.
- Hornillos, Valentin,Giannerini, Massimo,Vila, Carlos,Fananas-Mastral, Martin,Feringa, Ben L.
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supporting information
p. 5114 - 5117
(2013/10/22)
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- Room-temperature photoinduced direct C-H-arylation via base-promoted homolytic aromatic substitution
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Conceptually different approach toward biaryl syntheses by photoinduced direct C-H arylation of benzene and thiophene in the presence of t-BuOK is reported. The reaction proceeds through photo- and base-promoted homolytic aromatic substitution. The o-, m- and p- substituted ArI, as well as the electron-donating and electron-withdrawing nature of the substituents were found be good to excellent substrates. Heteroaryl, ArBr, ArCl and double C-H arylation were successfully achieved.
- Budén, María E.,Guastavino, Javier F.,Rossi, Roberto A.
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supporting information
p. 1174 - 1177
(2013/04/24)
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- Nickel-catalyzed cross-coupling of arene-or heteroarenecarbonitriles with aryl-or heteroarylmanganese reagents through C-CN bond activation
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The nickel-catalyzed cross-coupling reaction of arene- or heteroarenecarbonitriles with aryl- or heteroarylmanganese reagents via C-CN bond activation has been developed. Both electron-rich and electron-deficient nitriles can be employed as the electrophilic substrates. The reaction tolerates a range of functional groups and aromatic heterocycles. Copyright
- Liu, Ning,Wang, Zhong-Xia
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supporting information; experimental part
p. 1641 - 1645
(2012/07/31)
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- Polymer-supported syntheses of thiophene-containing compounds using a new type of traceless linker
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A new type of traceless linker is described for use in polymer-supported (PS) syntheses of thiophene-containing compounds. It is based on the cleavage of PS aryl 2-thienyl ketones by a mixture of potassium t-butoxide and water (typical mol ratio 10:3) in an ethereal solvent. Cleavage occurs to give the soluble thiophene-containing product. The method is used to prepare a range of eight thiophene-containing compounds including a terthiophene and a dialkylquaterthiophene. PS unsymmetrical diaryl ketones incorporating, for example, ortho-methoxyphenyl or pyrrole moieties could also serve as traceless linkers.
- Ben-Haida, Abderrazak,Hodge, Philip
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experimental part
p. 1754 - 1763
(2012/04/23)
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- Direct 2-arylation of thiophene using low loading of a phosphine-free palladium catalyst
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The direct coupling of aryl halides with thiophene would be a considerable advantage for sustainable development because of only HBr associated with a base as by-product is formed and the number of steps to prepare these compounds is less than in more cla
- Bensaid, Souhila,Roger, Julien,Beydoun, Kassem,Roy, David,Doucet, Henri
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experimental part
p. 3524 - 3531
(2011/09/16)
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- The 1,3-diaminobenzene-derived aminophosphine palladium pincer complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A highly active Suzuki-Miyaura catalyst with excellent functional group tolerance
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The rapidly prepared 1,3-diaminobenzenederived aminophosphine pincer complex {C6H3 [NHP(piperidinyl)2] 2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side-product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable. Experimental observations indicate that palladium nanoparticles are the catalytically active form of 1.
- Bolliger, Jeanne L.,Frech, Christian M.
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experimental part
p. 1075 - 1080
(2010/06/17)
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- Dichloro-bis(aminophosphine) complexes of palladium: Highly convenient, reliable and extremely active suzuki-miyaura catalysts with excellent functional group tolerance
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Dichloro-bis(aminophosphine) complexes are stable depot forms of palladium nanoparticles and have proved to be excellent SuzukiMiyaura catalysts. Simple modifications of the ligand (and/or the addition of water to the reaction mixture) have allowed their formation to be controlled. Dichlorobis[1- (dicyclohexylphosphany1)piperidine]palladium (3), the most active catalyst of the investigated systems, is a highly convenient, reliable, and extremely active Suzuki catalyst with excellent functional group tolerance that enables the quantitative coupling of a wide variety of activated, nonactivated, and deactivated and/or sterically hindered functionalized and heterocyclic aryl and benzyl bromides with only a slight excess (1.1-1.2 equiv) of arylboronic acid at 80°C in the presence of 0.2 mol % of the catalyst in technical grade toluene in flasks open to the air. Conversions of >95% were generally achieved within only a few minutes. The reaction protocol presented herein is universally applicable. Side-products have only rarely been detected. The catalytic activities of the aminophosphine-based systems were found to be dramatically improved compared with their phosphine analogue as a result of significantly faster palladium nanoparticle formation. The decomposition products of the catalysts are dicyclohexylphosphinate, cyclohexylphosphonate, and phosphate, which can easily be separated from the coupling products, a great advantage when compared with non-water-soluble phosphine-based systems.
- Bolliger, Jeanne L.,Frech, Christian M.
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experimental part
p. 4075 - 4081
(2010/08/05)
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- Decarboxylative cross-coupling of aryl tosylates with aromatic carboxylate salts
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(Figure Presented) A bimetallic copper/palladium catalyst system is disclosed that enables the use of tosylates as carbon electrophiles in decarboxylative coupling reactions. A variety of aromatic carboxylate salts, regardless of their substitution pattern, have been coupled with these inexpensive and readily available electrophiles to give the corresponding biaryl compounds in good yields (see scheme).
- Goossen, Luksa J.,Rodriguez, Nuria,Lange, Paul P.,Linder, Christophe
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supporting information; experimental part
p. 1111 - 1114
(2010/04/29)
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- Palladium-indolylphosphine-catalyzed hiyama cross-coupling of aryl mesylates
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(Chemical Equation Presented) Aryl mesylates are found to be applicable as electrophiles in organosilicon-mediated coupling reactions. The catalyst system comprising 2 mol % of Pd(OAc)2 and CM-phos supporting ligand is highly effective in catalyzing Hiyama cross-coupling of various aryl and heteroaryl mesylates. Interesting acid additive effects show that the presence of 0.25-0.50 equiv of acetic acid efficiently suppresses the mesylate decomposition and generally promotes the coupling product yields.
- So, Chau Ming,Lee, Hang Wai,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 317 - 320
(2009/07/04)
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- ORGANIC METAL COMPLEXES DERIVATIVE AND ORGANIC LIGHT EMITTING DEVICES USING THE SAME
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The present invention relates to a novel organic metal complex derivative and to an organic light emitting device comprising the same.
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Page/Page column 31
(2009/01/24)
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- An amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water
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(figure presented) The Suzuki-Miyaura coupling of aryl halides (8 varieties) and aryl-or vinylboronic acids (12 varieties) took place in water in the presence of a palladium complex of an amphiphilic polystyrene-poly(ethylene glycol) copolymer resin-supported N-anchored 2-aza-1,3-bis(diphenylphosphino)-propane ligand and potassium carbonate to give uniform and quantitative yields of the corresponding biaryls (96 varieties).
- Uozumi, Yasuhiro,Nakai, Yasushi
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p. 2997 - 3000
(2007/10/03)
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- PALLADIUM-CATALYZED ARYLATION OF FURAN, THIOPHENE, BENZOFURAN AND BENZOTHIOPHENE
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Treatment of ?-electron sufficient aromatic heterocycles such as furan, thiophene, benzofuran and benzothiophene with aryl bromides in the presence of tetrakis(triphenyphosphine)palladium gave the corresponding 2-aryl aromatic heterocycles.
- Ohta, Akihiro,Akita, Yasuo,Ohkuwa, Teruya,Chiba, Mari,Fukunaga, Ryuichi,et al.
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p. 1951 - 1958
(2007/10/02)
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- Palladium-Catalysed Coupling of Naphthyl Triflates with Organostannanes
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Naphthyl triflates undergo a palladium-catalysed coupling with organostannanes to give substituted naphthalenes.
- Crisp, Geoffrey T.,Papadopoulos, Spiros
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p. 1711 - 1716
(2007/10/02)
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- A Novel Friedel-Crafts Type Reaction of 2-Chlorothiophene with Some Active Aromatic Compounds
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2-Chlorothiophene (1) was found to easily react with certain active aromatic compounds (2) in the presence of AlCl3 under mild conditions, yielding the corresponding 2-arylthiophenes (3) and 5-chloro-2,2'-bithienyl (5) as the main products.With compounds more reactive than 1, the formation of 3 predominated.Reactions of 1 with aryl alkyl ethers, for example, afforded the corresponding 3 in 44-83percent yields in one step.
- Sone, Tyo,Yokoyama, Ryoji,Okuyama, Yohko,Sato, Kazuaki
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