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Alexander V. Akkuratov Fedor A. Prudnov Alexander V. Chernyak Petr M. Kuznetsov Alexander S. Peregudov Pavel A. Troshin 《Journal of polymer science. Part A, Polymer chemistry》2019,57(7):776-782
We report a facile synthesis of the well‐known and highly promising conjugated polymer TQ1 using eco‐friendly direct heteroarylation reaction. Optimization of the reaction conditions yielded the target polymer with good optoelectronic and charge‐transport characteristics. The TQ1 polymer obtained in the direct heteroarylation reaction delivered power conversion efficiency of ~5% in organic bulk heterojunction solar cells, which matches well the characteristics of the reference devices assembled using TQ1 batch synthesized via conventional Stille polycondensation reaction. The obtained results highlight the potential of the direct heteroarylation reaction as an efficient and environment‐friendly alternative to Stille cross‐coupling in the design of high‐quality semiconductor materials for organic electronics. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019 , 57, 776–782 相似文献
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Khalil Cherry Veronique Leclerc Pascal Carato Saïd Yous Pascal Berthelot 《Tetrahedron letters》2007,48(33):5751-5753
Several 5- and 6-acylindoles have been synthesized in good yield by means of palladium catalyzed cross-coupling reactions between acid chloride derivatives and 5- or 6-tributylstannylindoles to give useful intermediates for the synthesis of analogues of biologically and pharmacologically active molecules. 相似文献
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An efficient total synthesis of (±)-isocembrene via an intramolecular Stille cross-coupling reaction is described. A novel strategy towards the 1,3-diene-based cembrane-type macrocyclic diterpenoids has been realized. 相似文献
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Nora Carrera Ana C. Albéniz Pablo Espinet 《Journal of organometallic chemistry》2011,696(21):3316-3321
Stannylated polymers based on the polyfluorene backbone have been synthesized and used in the Stille reaction as recyclable reagents, minimizing the generation of toxic tin residues. 相似文献
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The Stille coupling of organostannanes and organohalides, mediated by air and moisture stable palladium(II) phosphine complexes containing succinimide or phthalimide (imidate) ligands, has been investigated. An efficient synthetic route to several palladium(II) complexes containing succinimide and phthalimide ligands, has been developed. cis-Bromobis(triphenylphosphine)(N-succinimide)palladium(II) [(Ph3P)2Pd(N-Succ)Br] is shown to mediate the Stille coupling of allylic and benzylic halides with alkenyl, aryl and allyl stannanes. In competition experiments between 4-nitrobromobenzene and benzyl bromide with a cis-stannylvinyl ester, (Ph3P)2Pd(N-Succ)Br preferentially cross-couples benzyl bromide, whereas with other commonly employed precatalysts 4-nitrobromobenzene undergoes preferential cross-coupling. Furthermore, preferential reaction of deactivated benzyl bromides over activated benzyl bromides is observed for the first time. The type of halide and presence of a succinimide ligand are essential for effective Stille coupling. The type of phosphine ligand is also shown to alter the catalytic activity of palladium(II) succinimide complexes. 相似文献
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Sreyashi Jana 《Tetrahedron letters》2009,50(34):4820-585
An efficient palladium(0) immobilized MCM-41 catalytic system for C-C cross-coupling reaction has been developed. Ligand-free Pd(0)-MCM-41 catalyst can be successfully used in coupling reaction between various aryl halides including deactivated chlorobenzene with aryl borane and organotin to give biaryls in excellent yields with high turnover frequency (TOF) (the maximal TOFs are up to 6990 for the reaction of bromobenzene with phenylboronic acid). The catalyst can be recycled and reused without any loss of catalytic activity. 相似文献
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This paper reports the synthesis of dineophyltin dihydride (3) following two procedures. The four steps synthesis starting from benzyl chloride and Sn was shown to be more convenient than the two step direct alkylation of SnCl4. The study of the free radical hydrostannation of mono- and disubstituted acetylenes with hydride 3 shows that they are stereoselective and that the stereoisomers obtained in higher proportion are stable and easily separated by column chromatography. Some preliminary studies on the chemical reactivity of the new divinylsubstituted dineophyltin compounds in Stille reactions are also informed. Radical hydrostannatation of (E)-trisubstituted ethylenes with 3 did not succeed probably due to steric factors. The preparation of dineophyltin bromohydride (27) is also reported. Radical addition of 27 to methyl (E)-2,3-disubstituted propenoates leads to mixtures of the corresponding erythro and threo adducts in diastereomeric excesses (d.e.) in the range of 74-90%. 相似文献
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Jean-Mathieu Chrétien Françoise Zammattio Erwan Le Grognec Gilles Montavon 《Tetrahedron letters》2007,48(10):1781-1785
The synthesis of two new vinyltin reagents grafted on an insoluble macroporous polymer is reported. These reagents were used in the palladium-catalyzed Stille cross-coupling reaction with aryl halides. In all reactions, the conversion of the starting aryl halide is high and the amount of organotin by-product is particularly low (at the end of the catalytic run, the amount of Sn is up to 16 ppm in the crude reaction mixture removed of the insoluble polymer, and it is less than 1 ppm in the product purified by chromatography on silica gel). 相似文献
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Anwesha Pal 《Tetrahedron》2010,66(29):5451-5458
Combination of 3,5-dimethyl-1-(2-(diphenylphosphino)phenyl)-1H-pyrazole, A, and 3-tert-butyl-5-methyl-1-(2-(diphenylphosphino)phenyl)-1H-pyrazole, B, with Pd2(dba)3 furnished excellent catalysts for Stille, Kumada and Hiyama cross-coupling reactions. Effects of solvents, bases and ligand/palladium ratio on efficiency of coupling reactions were studied. Molecular structures of palladium(II) complexes of A and B determined by single-crystal X-ray diffraction method revealed a close similarity of ligand arrangement around the metal centre. 相似文献
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Synthesis and X‐ray structural characterization of a bidendate phosphine (dppe) palladium(II) complex and its application in Stille and Suzuki cross‐coupling reactions
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Ali Naghipour Arash Ghorbani‐Choghamarani Heshmatollah Babaee Behrouz Notash 《应用有机金属化学》2016,30(12):998-1003
The synthesis, characterization, crystal structure and catalyst activity of the bidentate phosphine complex [1,2‐bis(diphenylphosphino)ethane]palladium(II) bromide, [PdBr2(dppe)], are presented. Treatment of 1,2‐bis(diphenylphosphino)ethane with palladium(II) bromide under mild conditions resulted in the compound in high yield and purity. The characterization of the synthesized compound was performed using spectroscopic methods, such as Fourier transform infrared and NMR, CHN analysis and X‐ray crystallography. The structure of the compound was slightly distorted square planar. This compound was found to work as an efficient catalyst for both Stille and Suzuki cross‐coupling reactions of various aryl halides with triphenyltin chloride and/or phenylboronic acid. Also, the catalyst could be recovered and reused several times without significant loss of its catalytic activity. Copyright © 2016 John Wiley & Sons, Ltd. 相似文献
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Marius Hervé Dr. Guillaume Lefèvre Dr. Emily A. Mitchell Prof. Bert U. W. Maes Dr. Anny Jutand 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(50):18401-18406
The mechanism of Stille reactions (cross‐coupling of ArX with Ar′SnnBu3) performed in the presence of fluoride ions is established. A triple role for fluoride ions is identified from kinetic data on the rate of the reactions of trans‐[ArPdBr(PPh3)2] (Ar=Ph, p‐(CN)C6H4) with Ar′SnBu3 (Ar′=2‐thiophenyl) in the presence of fluoride ions. Fluoride ions promote the rate‐determining transmetallation by formation of trans‐[ArPdF(PPh3)2], which reacts with Ar′SnBu3 (Ar′=Ph, 2‐thiophenyl) at room temperature, in contrast to trans‐[ArPdBr(PPh3)2], which is unreactive. However, the concentration ratio [F?]/[Ar′SnBu3] must not be too high, because of the formation of unreactive anionic stannate [Ar′Sn(F)Bu3]?. This rationalises the two kinetically antagonistic roles exerted by the fluoride ions that are observed experimentally, and is found to be in agreement with the kinetic law. In addition, fluoride ions promote reductive elimination from trans‐[ArPdAr′(PPh3)2] generated in the transmetallation step. 相似文献
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An efficient catalytic system using (BeDABCO)2Pd2Cl6 was developed for the Stille cross‐coupling reaction. The substituted biaryls were produced in excellent yields in short reaction times using a catalytic amount of this catalyst in DMF at 120 °C. The ionic character of homogeneous catalyst and microwave irradiation and also DMF as microwave‐active polar solvent gave higher yields and shorter reaction times than conventional heating. Benzyl DABCO as an efficient ligand and also a quaternary ammonium salt had an efficient stabilizing effect on the Pd(0) species. Copyright © 2013 John Wiley & Sons, Ltd. 相似文献
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Intramolecular trans‐Dicarbofunctionalization of Alkynes by a Formal anti‐Carbopalladation/Stille Cascade
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Bastian Milde Andreas Reding Finn J. Geffers Prof. Dr. Peter G. Jones Prof. Dr. Daniel B. Werz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(41):14544-14547
An intramolecular Pd‐catalyzed trans‐dicarbofunctionalization of internal alkynes using aryl bromides and aryl stannanes is presented. Tetrasubstituted double bonds embedded in an oligocyclic ring system are obtained in a regio‐ and diastereoselective fashion. The transformation features a broad substrate scope and functional‐group tolerance. 相似文献
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炔基砜和三丁基锡化氢在四(三苯基膦)钯催化下于苯中室温下进行锡氢化反应4 h,经溶剂转换成DMF后,再在CuI助催化剂存在下与炔基溴化物于室温进行Stille偶联反应,以良好产率且立体选择性地合成了( Z)-2-砜基取代的1,3-烯炔。该“一锅”合成法具有起始原料易得、反应条件温和、操作简便、钯催化剂利用率高和产率好等优势。 相似文献
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The Stille cross‐coupling reaction of organostannanes with aryl halides was achieved in the presence of a catalytic amount of MCM‐41‐supported mercapto palladium(0) complex (1 mol%) in DMF? H2O (9:1) under air atmosphere in good to high yields. This MCM‐41‐supported palladium catalyst can be reused at least 10 times without any decrease in activity. Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
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Katarzyna B?a?ewska 《Tetrahedron》2004,60(51):11701-11707
An efficient completely diastereoselective synthesis of (Z)- and (E)- N-Boc 1-aminoalkenylphosphonic acid diethyl esters from easily available 5-substituted (2-thioxo-oxazolidin-4-yl)phosphonic acid diethyl esters has been developed. 相似文献
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A Stille coupling reaction of organostannanes with organic halides has been developed in the presence of a catalytic amount of MCM-41-supported bidentate phosphine palladium(0) complex (0.5 mol %) in DMF/H2O (9:1) under air atmosphere in high yields. This polymeric palladium catalyst exhibits higher activity than Pd(PPh3)4 and can be reused at least 10 times without any decrease in activity. 相似文献