cas 86521-05-3, 2-(TRIMETHYLSILYLETHYNYL)PYRIDINE

Articles about 86521-05-3Total 42 be found

Article title
Article abstract
Author
Journal number and time
Download

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide
Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.
Kumaki, Wataru,Kinoshita, Hidenori,Miura, Katsukiyo
supporting information

(2022/03/07)

Experimental and theoretical investigations into the manifestation of the γ-effect in 2- and 4-[2-silylethyl)]pyridines and pyridinium ions
The γ-effect of the group 14 metals is a stabilizing interaction involving the back-lobe of the σC-M (M = Si, Ge, Sn, Pb) interacting with the developing carbocation γ to the tetrel. This percaudal interaction has been observed in solvolysis experiments with significant rate enhancements over unsubstituted systems, and subsequent isolation of three-membered ring products. In this study, the γ-effect is experimentally investigated in the solid phase with X-ray crystallography, the solution phase with Si-C coupling constants, and the gas phase via collision-induced dissociation (CID). Moving from 2- and 4-silylethyl substituted pyridines to the more electron demanding substituted pyridinium ion systems results in systematic shifts in key structural parameters including the 29Si-13C NMR coupling constants consistent with the cyclopropane-like resonance form attributable to the γ-effect. However, these shifts are much less in magnitude than those previously reported for the well documented β-effect. The gas phase CID results also reflect this with the fragmentation pathways for the silylethyl substituted systems not being dominated by the percaudal interaction, compared to previous studies where all major fragments were attributable to the β-effect. Density functional theory (DFT) calculated hyperhomodesmotic equations in combination with natural bond orbital (NBO) theory also supported the experimental trends with the γ-effect providing stabilization in the pyridinium ion systems studied, but to a much smaller extent to the β-effect.
Karnezis, Asimo,Brydon, Samuel C.,Molino, Andrew,Wilson, David J.D.,O'Hair, Richard A.J.,White, Jonathan M.
supporting information

(2021/09/08)

Ru(II) coordination compounds of N[sbnd]N bidentate chelators with 1,2,3 triazole and isoquinoline subunits: Synthesis, spectroscopy and antimicrobial properties
Bidentate chelators 1-(1-benzyl-1,2,3-triazol-4-yl)isoquinoline and 3-(1-benzyl-1,2,3-triazol-4-yl)isoquinoline were prepared from benzyl bromide and trimethylsilylethynylisoquinoline precursors using a tandem deprotection/substitution/CuAAC synthetic approach. Each chelator is capable of forming a stable 3:1 Ru(II) coordination compound, which forms as a geometric isomer mixture. These Ru(II) complexes possess unique MLCT absorbance signatures at 450/472 nm (1-isomer) and 367 nm (3-isomer) relative to their constituent chelating units. Minimum inhibitory concentration values as low as 0.4 μM are observed for Ru(II) complexes against representative Gram-positive bacteria Bacillus subtilis and Staphylococcus epidermidis. Comparing the MIC values of these isoquinoline compounds with analogous 2-(1-benzyl-1,2,3-triazol-4-yl)pyridine compounds shows a 2.5- to 40-fold improvement in potency. This study establishes that increased hydrophobicity introduced at the central chelating units of Ru(II) coordination compounds can be a useful means by which to optimize antimicrobial activity that is complimentary to the variation of peripheral substituent identity at the chelator's N1 triazole position.
Kreofsky, Nicholas W.,Dillenburg, Maxwell D.,Villa, Eric M.,Fletcher, James T.
supporting information

(2019/12/26)

The synthesis of cyclometalated platinum(ii) complexes with benzoaryl-pyridines as C^N ligands for investigating their photophysical, electrochemical and electroluminescent properties
A series of (C^N)Pt(acac)-type complexes has been successfully synthesized with a benzo[b]furan, benzo[b]thiophene, benzo[b]selenophene, or benzo[b]tellurophene group in the benzoaryl-pyridine ligand. Using X-ray crystallography, the chemical structures o
Wang, Dezhi,Chen, Xi,Yang, Hua,Zhong, Daokun,Liu, Boao,Yang, Xiaolong,Yue, Ling,Zhou, Guijiang,Ma, Miaofeng,Wu, Zhaoxin
supporting information
p. 15633 - 15645
(2020/11/24)

Palladium (II) complexes chelated by 1-substituted-4-pyridyl-1H-1,2,3-triazole ligands as catalyst precursors for selective ethylene dimerization
A series of neutral as well as cationic palladium methyl complexes bearing 1-substituted-4-pyridyl-1H-1,2,3-triazole ligands were prepared and fully characterized by a range of analytical techniques. Conventional and 2D NMR spectroscopy as well as single-crystal X-ray diffraction analysis unambiguously determined the molecular structure of the complexes. The neutral complexes activated by methylaluminoxane were found to be effective catalysts in the ethylene dimerization reaction. The catalyst performance of the in-situ-generated active species was compared with the discrete cationic complexes of the same ligand scaffold. Activities and selectivities for the two systems were remarkably similar, pointing to similarities in the nature of the active species. Both catalytic systems showed a strong correlation of activity and selectivity with the nature of the ligand scaffold. Highest activities were attained when electron-withdrawing groups were incorporated into the triazole ring, while increasing steric bulk in the ortho-position on the pyridyl ring of the ligand led to the almost exclusive dimerization of ethylene with selectivities up to 94% observed toward 1-butene.
Joseph, Mohammed Cassiem,Swarts, Andrew John,Mapolie, Selwyn Frank
(2020/03/03)

RET INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
Provided herein are a RET inhibitor, a pharmaceutical composition thereof and uses thereof. In particular, provided is a compound having Formula (I) or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof. Provided is a pharmaceutical composition comprising the compound, and uses of the compound and pharmaceutical composition thereof for the preparation of a medicament, in particular for treatment and prevention of RET-related diseases and conditions, including cancer, irritable bowel syndrome, and/or pain associated with irritable bowel syndrome.
-
Paragraph 00230; 00316; 00378

(2020/07/05)

BTK Inhibitors and uses thereof
The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.
-
Paragraph 1600-1605

(2020/05/02)

Design and characterization of a heterocyclic electrophilic fragment library for the discovery of cysteine-targeted covalent inhibitors
A fragment library of electrophilic small heterocycles was characterized through cysteine-reactivity and aqueous stability tests that suggested their potential as covalent warheads. The analysis of theoretical and experimental descriptors revealed correlations between the electronic properties of the heterocyclic cores and their reactivity against GSH that are helpful in identifying suitable fragments for cysteines with specific nucleophilicity. The most important advantage of these fragments is that they show only minimal structural differences from non-electrophilic counterparts. Therefore, they could be used effectively in the design of targeted covalent inhibitors with minimal influence on key non-covalent interactions.
Keeley,ábrányi-Balogh,Keseru
supporting information
p. 263 - 267
(2019/03/05)

Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis
Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido comple
Chiu, Hsin-Chun,Tonks, Ian A.
supporting information
p. 6090 - 6094
(2018/05/30)

Microwave-assisted copper- and palladium-catalyzed sonogashira-type coupling of aryl bromides and iodides with trimethylsilylacetylene
An efficient and rapid method was developed for the synthesis of 1-aryl-2-(trimethylsilyl)acetylene. Copper and palladium-catalyzed sonogashira-type coupling of trimethylsilylacetylene and aryl bromides or iodides in the presence of triethylamine as base
Lei, Yonghua,Hu, Tianhan,Wu, Xingsen,Wu, Yue,Xiang, Hua,Sun, Haopeng,You, Qidong,Zhang, Xiaojin
p. 1100 - 1103
(2016/03/09)

Synthesis and structural studies of 1,4-di(2-pyridyl)-1,2,3-triazole dpt and its transition metal complexes; A versatile and subtly unsymmetric ligand
The synthesis of the 'click' derived 1,4-di(2-pyridyl)-1,2,3-triazole (dpt) chelator/ligand from 2-azidopyridine and 2-ethynylpyridine using Cu(i) and TBTA by microwave assisted synthesis is presented. The complexes of the subtly unsymmetric dpt ligand with Cu(i), Pt(ii), Co(ii), and Ag(i) were structurally characterised by using conventional methods, as well as using single crystal and powder diffraction analysis. The results of the studies showed formation of discrete molecules displaying preferential binding of the d-metal cations through the pyridyl nitrogen N1 and the proximal triazolyl nitrogen N2 i.e. the 2-(1H-1,2,3-triazol-4-yl)pyridine or 'regular' chelate moiety despite the presence of a second potential binding pocket i.e. the 2-(1H-1,2,3-triazol-1-yl)pyridine chelate or 'inverse' moiety. This binding selectivity was corroborated through the study of the self-assembly of dpt with Cu(i) and Ag(i) using 1H NMR titration in CD3CN solution, as well as using UV-Vis absorption titrations; the former showing a broadening of the proton peaks associated with that chelate pocket.
McCarney, Eoin P.,Hawes, Chris S.,Blasco, Salvador,Gunnlaugsson, Thorfinnur
supporting information
p. 10209 - 10221
(2016/07/06)

A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines
The addition of InBr3 to the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane led to a dramatic increase in the reactivity to afford the corresponding 1,3-enynes bearing a trifluoromethyl group on their terminal sp2 carbon. The subsequent cyclization of these 1,3-enynes under palladium catalysis provides access to the corresponding indoles bearing a 3,3,3-trifluoroprop-1-enyl group at their 2-position.
Ikeda,Omote,Kusumoto,Komori,Tarui,Sato,Ando
supporting information
p. 2127 - 2133
(2016/02/18)

The Role of Substituent Effects in Tuning Metallophilic Interactions and Emission Energy of Bis-4-(2-pyridyl)-1,2,3-triazolatoplatinum(II) Complexes
The photoluminescence spectra of a series of 5-substituted pyridyl-1,2,3-triazolato PtII homoleptic complexes show weak emission tunability (ranging from λ=397-408 nm) in dilute (10-6 M) ethanolic solutions at the monomer level and strong tunability in concentrated solutions (10-4 M) and thin films (ranging from λ=487-625 nm) from dimeric excited states (excimers). The results of density functional calculations (PBE0) attribute this "turn-on" sensitivity and intensity in the excimer to strong Pt-Pt metallophilic interactions and a change in the excited-state character from singlet metal-to-ligand charge transfer (1MLCT) to singlet metal-metal-to-ligand charge transfer (1MMLCT) emissions in agreement with lifetime measurements. Turn-on tunability: A series of bis-4-(2-pyridyl)-1,2,3-triazolatoplatinum(II) complexes display variable emission tunability. At low concentration, the emission can be tuned only slightly by changing the nature of the substituent but at higher concentrations tunability is enhanced. This "turn-on" sensitivity in the excimeric emission is attributed to strong Pt-Pt metallophilic interactions and a change in the excited-state character.
Prabhath, M. R. Ranga,Romanova, Julia,Curry, Richard J.,Silva, S. Ravi P.,Jarowski, Peter D.
supporting information
p. 7949 - 7953
(2015/06/30)

Rapid and efficient desilylation and deuteration of alkynylpyridines
We describe a rapid and efficient technique for the direct installation of deuterium atoms following the removal of trimethylsilyl groups from alkynylpyridines. Utilizing tetrabutylammonium fluoride in the presence of deuterium oxide, we observe up to 97% deuterium incorporation in as little as one minute of reaction time.
Gelinas, Benjamin S.,Jaye, Joseph A.,Mattos, Gabriela R.,Fort, Eric H.
supporting information
p. 4232 - 4233
(2015/06/22)

3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine capped Pd(0) nanoparticles: A catalyst for copper-free Sonogashira coupling of aryl halides in aqueous medium
3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) capped Pd(0) nanoparticles (TzPdNPs) as a catalyst in the Sonogashira coupling of aryl halides in aqueous medium with diminished homocoupling is reported. The methodology provides a facile route to obtain polyfunctional alkynes under ligand- and copper-free conditions. The procedure is also efficient for aryl chlorides.
Das, Sudipto,Samanta, Suvendu,Ray, Shounak,Biswas, Papu
p. 75263 - 75267
(2015/09/21)

MGLUR REGULATORS
Provided herein are compounds of the formula I: (I), as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment or prevention of mGluR5 mediated disorders, such as acute and/or chronic neurological disorders, cognitive disorders and memory deficits, as well as acute and chronic pain.
-
Page/Page column 35

(2014/09/03)

NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions
An organo-catalytic protocol for the trimethylsilylation of terminal alkynes employing Ruppert's reagent (CF3SiMe3) as a trimethylsilyl source has been developed under solvent and fluoride free conditions. This method was found to be very effective as a variety of terminal alkynes bearing aliphatic or aromatic substituents underwent smooth transformation to their corresponding silylated products in excellent yields within a few minutes using N-heterocyclic carbene as an organo-catalyst. This methodology was also applied to the chemospecific N-silylation of indoles. This journal is
Arde, Panjab,Reddy, Virsinha,Anand, Ramasamy Vijaya
p. 49775 - 49779
(2014/12/11)

Efficient synthesis of 2-pyridylenynes and application in cobalt-catalysed benzannulation reactions
The cobalt-catalysed benzannulation of 2-pyridine-substituted enynes gave 2,3-bis(2-pyridyl)styrenes in moderate yields. The reaction with dibromomethane as well as diiodomethane generated the corresponding planar-chiral bispyridinium salts in good yields
R?se, Philipp,Pünner, Florian,Hilt, Gerhard,Harms, Klaus
p. 1101 - 1104
(2013/06/27)

Palladium-catalyzed oxidative homocoupling reaction of terminal acetylenes using trans-bidentatable 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene
Palladium-catalyzed oxidative homocoupling of terminal acetylenes, in air, occurred in the presence of 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene as ligand, affording the corresponding conjugated diynes.
Atobe, Shingo,Sonoda, Motohiro,Suzuki, Yuki,Yamamoto, Takuya,Masuno, Haruna,Shinohara, Hiroyuki,Ogawa, Akiya
p. 359 - 370
(2013/03/28)

Rapid discovery of a novel series of Abl kinase inhibitors by application of an integrated microfluidic synthesis and screening platform
Drug discovery faces economic and scientific imperatives to deliver lead molecules rapidly and efficiently. Using traditional paradigms the molecular design, synthesis, and screening loops enforce a significant time delay leading to inefficient use of data in the iterative molecular design process. Here, we report the application of a flow technology platform integrating the key elements of structure-activity relationship (SAR) generation to the discovery of novel Abl kinase inhibitors. The platform utilizes flow chemistry for rapid in-line synthesis, automated purification, and analysis coupled with bioassay. The combination of activity prediction using Random-Forest regression with chemical space sampling algorithms allows the construction of an activity model that refines itself after every iteration of synthesis and biological result. Within just 21 compounds, the automated process identified a novel template and hinge binding motif with pIC50 > 8 against Abl kinase - both wild type and clinically relevant mutants. Integrated microfluidic synthesis and screening coupled with machine learning design have the potential to greatly reduce the time and cost of drug discovery within the hit-to-lead and lead optimization phases.
Desai, Bimbisar,Dixon, Karen,Farrant, Elizabeth,Feng, Qixing,Gibson, Karl R.,Van Hoorn, Willem P.,Mills, James,Morgan, Trevor,Parry, David M.,Ramjee, Manoj K.,Selway, Christopher N.,Tarver, Gary J.,Whitlock, Gavin,Wright, Adrian G.
supporting information
p. 3033 - 3047
(2013/05/22)

OXAZOLIDINONES AS MODULATORS OF MGLUR5
The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands, agonists and partial agonists for the mGluR5 receptor and may be useful for the treatment of various disorders of the central nervous system.
-
Page/Page column 60-61

(2012/05/31)

Rapid consecutive three-component coupling-Fiesselmann synthesis of luminescent 2,4-disubstituted thiophenes and oligothiophenes
(Hetero)aroyl chlorides, alkynes, and ethyl 2-mercapto acetate can be reacted in a consecutive three-component synthesis to give 2,4-disubstituted thiophene 5-carboxylates in good to excellent yields. In the sense of a pseudo-five-component reaction highly blue luminescent symmetrical terthiophenes and a quinquethiophene can be synthesized in excellent yield.
Teiber, Marco,Mueller, Thomas J. J.
supporting information; experimental part
p. 2080 - 2082
(2012/03/10)

Metal-free 1,5-regioselective azide-alkyne [3+2]-cycloaddition
[3+2]-cycloaddition reactions of aromatic azides and silylated alkynes in aqueous media yield 1,5-disubstituted-4-(trimethyl-silyl)-1H-1,2,3-triazoles. The formation of the 1,5-isomer is highly favored in this metal-free cycloaddition, which could be proven by 1D selective NOESY and X-ray investigations. Additionally, DFT calculations corroborate the outstanding favoritism regarding the 1,5-isomer. The described method provides a simple alternative protocol to metal-catalyzed "click chemistry" procedures, widening the scope for regioselective heavy-metal-free synthetic applications.
Kloss, Florian,Koehn, Uwe,Jahn, Burkhard O.,Hager, Martin D.,Goerls, Helmar,Schubert, Ulrich S.
supporting information; experimental part
p. 2816 - 2824
(2012/06/01)

One-pot click synthesis of 1N-alkyl-4-aryl-1,2,3-triazoles from protected arylalkynes and alkyl bromides
1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes. Georg Thieme Verlag Stuttgart. New York.
Ladouceur, Sebastien,Soliman, Ahmed M.,Zysman-Colman, Eli
supporting information; experimental part
p. 3604 - 3611
(2011/12/16)

Copper-free sonogashira coupling reaction using a trans-spanning 1,2-Bis(2-thienylethynyl)benzene Ligand
Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl) benzene (1) as a trans-bidentatable ligand.
Atobe, Shingo,Sonoda, Motohiro,Suzuki, Yuki,Shinohara, Hiroyuki,Yamamoto, Takuya,Ogawa, Akiya
supporting information; experimental part
p. 925 - 927
(2011/12/05)

Potent mGluR5 antagonists: Pyridyl and thiazolyl-ethynyl-3,5-disubstituted- phenyl series
We report the synthesis of four series of 3,5-disubstituted-phenyl ligands targeting the metabotropic glutamate receptor subtype 5: (2-methylthiazol-4-yl) ethynyl (1a-j,), (6-methylpyridin-2-yl)ethynyl (2a-j), (5-methylpyridin-2-yl) ethynyl (3a-j,), and (pyridin-2-yl)ethynyl (4a-j,). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro assay. All compounds were found to be full antagonists and exhibited low nanomolar to subnanomolar activity.
Alagille, David,Dacosta, Herve,Chen, Yelin,Hemstapat, Kamondanai,Rodriguez, Alice,Baldwin, Ronald M.,Conn, Jeffrey P.,Tamagnan, Gilles D.
scheme or table
p. 3243 - 3247
(2011/07/07)

One-pot procedure for the synthesis of unsymmetrical diarylalkynes
Unsymmetrical diarylalkynes are accessible by a one-pot procedure from two different aryl halides and (trimethylsilyl)acetylene. The three-component coupling is initialized by a Pd/Cu-catalyzed Sonogashira coupling of an aryl halide with (trimethylsilyl)a
Severin, Rene,Reimer, Jessica,Doye, Sven
supporting information; experimental part
p. 3518 - 3521
(2010/07/17)

High-efficiency solution processable electrophosphorescent iridium complexes bearing polyphenylphenyl dendron ligands
We report the synthesis and electrophosphorescent behavior of a series of novel iridium complex materials (Complexes A-F), which are composed of ligands bearing polyphenylphenyl dendron groups and acetylacetonate. Yellow to saturated red organic light-emitting diodes (OLEDs) based on these newly developed Ir complexes were fabricated through solution process by doping the complex materials into polyvinyl carbazole (PVK)/2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD) matrices. The emission wavelengths of the materials could be effectively tuned from 549 nm to 640 nm by changing the conjugation of the ligands either through incorporating additional aromatic segment (e.g. phenyl or fluorenyl group) onto the basic dendron ligand or fusing two of the phenyl rings on the polyphenylphenyl dendron group. High performance devices with the configuration of ITO/poly(3,4-ethylenedioxythiophene):poly(styrenesulfonic acid) (PEDOT:PSS) (50 nm)/PVK:PBD (40%):Ir complex (6%) (70 nm)/2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) (12 nm)/Alq3 (20 nm)/Mg:Ag (150 nm) have been demonstrated. For example, when Complex B was used as the emissive layer, maximum current efficiency of 34.0 cd/A and external quantum efficiency of 10.3% have been achieved. When 1,3,5-tris(N-phenylbenzimidazol-2-yl) benzene (TPBI) was used as the block layer, the efficiencies can be further improved to 46.3 cd/A and 13.9%, respectively. These solution processed OLED devices demonstrated quite stable EL efficiencies over a large range of current density, which indicated that triplet-triplet annihilation in electrophosphorescence could be effectively suppressed by incorporation of the polyphenylphenyl dendron structure into iridium complexes.
Huang, Chun,Zhen, Chang-Gua,Su, Siew Ping,Chen, Zhi-Kuan,Liu, Xiao,Zou, De-Chun,Shi, Yan-Rong,Loh, Kian Ping
experimental part
p. 1317 - 1324
(2009/09/06)

The sequential Sonogashira-click reaction: A versatile route to 4-aryl-1,2,3-triazoles
Aryl halides can be easily transformed in a one-pot procedure into 4-aryl-1,2,3-triazoles with palladium/copper-catalyzed Sonogashira-click reaction sequence, using trimethylsilylacetylene as acetylene surrogate.
Loerincz, Krisztian,Kele, Peter,Novak, Zoltan
experimental part
p. 3527 - 3532
(2010/02/28)

Blue fluorescent 4a-aza-4b-boraphenanthrenes
Figure presented Phenanthrene analogues with internalized B-N moieties were found to afford blue light emission with good quantum efficiencies, whereas the isomeric species with peripheral B-N moieties displayed only UV emission behavior, like the all-carbon framework.
Bosdet, Michael J. D.,Jaska, Cory A.,Piers, Warren E.,Sorensen, Ted S.,Parvez, Masood
p. 1395 - 1398
(2007/12/31)

SOLUTION PROCESSED ORGANOMETALLIC COMPLEXES AND THEIR USE IN ELECTROLUMINESCENT DEVICES
The invention provides phosphorescent organometallic complexes. The complexes of the invention may be prepared as films further comprising a charge carrying host material may be used at an emissive layer in organic light emitting devices. In one embodiment, the complex is a hyper-branched organoiridium complex comprising a 2-phenylpuridine ligand wherein the phenyl ring or the pyridine ring contains 4 non-hydrogen substituents. In another embodiment, the complex is an organoiridium complex comprising a substituted 2-phenyl pyridine ligand, wherein at least one substituent contains a spiro group.
-
Page/Page column 28

(2008/06/13)

Double elimination protocol for the synthesis of arylene ethynylenes containing heteroaromatic rings
The double elimination reaction of β-substituted sulfones offers a versatile strategy for synthesis of arylene ethynylene kits containing heteroaromatic rings. A sequence of aldol reaction between α-sulfonyl carbanion and aldehyde, trapping the resulting aldolate to give β-substituted sulfone, and double elimination of this intermediate can be integrated in one pot. This protocol allows thiophene, pyridine, and ferrocene units to be accommodated in phenylene ethynylene arrays.
Orita, Akihiro,Ye, Fangguo,Babu, Govindarajulu,Ikemoto, Tomohiro,Otera, Junzo
p. 716 - 727
(2007/10/03)

Triplet acetylenes as synthetic equivalents of 1,2-bicarbenes: Phantom n,π* state controls reactivity in triplet photocycloaddition
Diaryl acetylenes, in which one of the aryl groups is either a pyridine or a pyrazine, undergo efficient triplet state photocycloaddition to 1,4-cyclohexadiene with formation of 1,5-diaryl substituted tetracyclo[3.3.0. 02,8.04,6]octa
Zeidan, Tarek A.,Kovalenko, Serguei V.,Manoharan, Mariappan,Clark, Ronald J.,Ghiviriga, Ion,Alabugin, Igor V.
p. 4270 - 4285
(2007/10/03)

Efficient synthesis of a complete donor/acceptor bis(aryl)diyne family
A facile route to a family of bis(aryl)diynes containing both an electron donating pyridine ring and an electron accepting iodobenzene has been developed. The convergent synthesis involves the coupling of 2-, 3-, or 4-bromopyridine with TMS-acetylene, followed by deprotection to form the first half of the molecule. Similarly, 2-, 3-, or 4-iodoaniline was coupled to TMS-acetylene after protection of the amine group as a diethyltriazine. After conversion of the triazine to an iodine, deprotection of the acetylene and formation of the corresponding bromophenyl-acetylene, the two halves of the molecule were coupled under Cadiot-Chodkiewicz conditions. Nine new compounds were prepared, each of which was found to thermally polymerize from the melt. None of the compounds underwent photochemical polymerization in the solid-state.
Holmes, Brian T.,Pennington, William T.,Hanks, Timothy W.
p. 2447 - 2461
(2007/10/03)

Synthesis and characterization of 2,5-bis(2-pyridyl)thiophene
2-[2-(Trimethylsilyl)ethynyl] pyridine (6) was prepared in 95% yield by reaction of 2-bromopyridine with trimethylsilylacetylene in triethylamine in the presence of bis(triphenylphosphine)Palladium(II) chloride and Copper(I) iodide. Desilylation of (6) by refluxing with sodium hydroxide in methanol (yield 95%) of 2-ethynylpyridine (5). Oxidative coupling of (5) in pyridine by oxygen in the presence of Copper(I) chloride gives 70% yield of 1,4-bis(2-pyridyl)1,3-butadiyne (4). Reaction of 4 with sodium sulfide affords 100% of 2,5-bis(2-pyridyl) thiophene (1).
Al-Taweel, Samir A.
p. 1041 - 1045
(2007/10/03)

Synthesis of diterpenoid indole derivatives via tethered chromium alkynylaminocarbenes
Thermolysis of podocarpane-tethered chromiumalkynylaminocarbenes gives indole derivatives in moderate yields. (Arylalkynyl)aminocarbenes could not be isolated. Ester derivatives were formed due to trapping of the intermediate ketene in situ with butan-1-o
Woodgate, Paul D.,Sutherland, Hamish S.
p. 131 - 144
(2007/10/03)

Synthesis and preliminary testing of molecular wires and devices
Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups for attachment to numerous metal probes and surfaces are presented. Some of the functionalized molecular systems showed linear, wire-like, current versus voltage (I(V)) responses, while others exhibited nonlinear I(V) curves for negative differential resistance (NDR) and molecular random access memory effects. Finally, the syntheses of functionalized oligomers are described that can form self-assembled monolayers on metallic electrodes that reduce the Schottky barriers. Information from the Schottky barrier studies can provide useful insight into molecular alligator clip optimizations for molecuar electronics.
Tour, James M.,Rawlett, Adam M.,Kozaki, Masatoshi,Yao, Yuxing,Jagessar, Raymond C.,Dirk, Shawn M.,Price, David W.,Reed, Mark A.,Zhou, Chong-Wu,Chen, Jia,Wang, Wenyong,Campbell, Ian
p. 5118 - 5134
(2007/10/03)

Rapid homogeneous-phase sonogashira coupling reactions using controlled microwave heating
A microwave-enhanced, rapid and efficient homogeneous-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides, bromides, triflates, and aryl chloride, as well as pyridine and thiophene derivatives with t
Erdelyi,Gogoll
p. 4165 - 4169
(2007/10/03)

Palladium-catalyzed coupling of heteroaromatic triflates with acetylene and its application for a dynemicin A intermediate
An acetylene moiety was introduced to a carbonyl carbon of amide group via its triflate in the presence of palladium catalyst. The reaction proceeded smoothly under mild conditions. Utilizing this methodology, a model compound of dynemicin A bearing acety
Okita, Takaaki,Isobe, Minoru
p. 3737 - 3744
(2007/10/02)

Cross-Coupling Reactions of Monosubstituted Acetylenes and Aryl Halides Catalysed by Palladium on Charcoal
A convenient procedure for the Pd(O) catalyzed cross-coupling of monosubstituted acetylenes with aryl halides, in which palladium on charcoal serves as the source of the noble metal, is described.
Rosa, Martha A. De la,Velarde, Esperanza,Guzman, Angel
p. 2059 - 2064
(2007/10/02)

REGIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED PYRIDINES VIA GRIGNARD ADDITION TO 1-(ALKOXYCARBOXY)-PYRIDINIUM SALTS
A regioselective one pot synthesis of 2-substituted pyridine derivatives from pyridine-1-oxides is described.
Webb, Thomas R.
p. 3191 - 3194
(2007/10/02)

A Facile Synthesis of Ethynyl-Substituted Six-Membered N-Heteroaromatic Compounds
-
Sakamoto, Takao,Shiraiwa, Masafumi,Kondo, Yoshinori,Yamanaka, Hiroshi
p. 312 - 314
(2007/10/02)