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1.
We report here a fast, easy, and efficient method for the preparation of aryl nitriles from aryl bromides and chlorides. The methodology for aryl bromides involves the use of either Ni(CN)(2) or NaCN and NiBr(2). With aryl chlorides, a mix of NaCN and NiBr(2) is used and the reaction proceeds via the in situ formation of the corresponding aryl bromide. The reaction can be performed in air and is complete within 10 min. 相似文献
2.
[reaction: see text] An efficient Pd(OAc)2/Dabco-catalyzed Stille cross-coupling reaction procedure has been developed. In the presence of Pd(OAc)2 and Dabco (triethylenediamine), various aryl halides including aryl iodides, aryl bromides, and activated aryl chlorides were coupled efficiently with organotin compounds to afford the corresponding biaryls, alkene, and alkynes in good to excellent yields. Furthermore, high TONs [turnover numbers, up to 980,000 TONs for the coupling reaction of 1-bromo-4-nitrobenzene and furan-2-yltributyltin] for the Stille cross-coupling reaction were observed. 相似文献
3.
The scope and limitations of the transition-metal-free Suzuki-type coupling of aryl halides and arylboronic acids to form biaryls are presented. Confirmation that the reaction is indeed metal-free is presented. The effects of changing base, solvent, reaction temperature, phase-transfer catalyst, and substrate are shown and the implications of these results discussed in terms of their impact on the synthetic versatility of the methodology. The main findings are that the reaction works well for aryl bromides, water is necessary as a solvent for the reaction, the optimum temperature for the reaction is 150 degrees C, the reaction is best performed by using microwave promotion with the exception of an electron-poor aryl bromide example where conventional heating may be used, only limited boronic acids can be used as coupling partners, sodium carbonate is the best base for the reaction, tetrabutylammonium bromide proves to be the best phase-transfer catalyst for the reaction, the reaction is limited to couplings between aryl halides and aryl boronic acids with sp(2)-sp(3) couplings proving ineffective, and NaBPh(4) can be used in the place of phenylboronic acid as a phenylating agent. 相似文献
4.
[reaction: see text] The coupling reaction of germanium compounds with aryl halides has been developed. The Pd(0)-catalyzed reaction of aryl halides with tri(2-furyl)germane provides aryltri(2-furyl)germanes in good yield. The cross-coupling reaction of aryltri(2-furyl)germanes with aryl halides is achieved. This allows facile synthesis of unsymmetrical biaryls from two different aryl halides. 相似文献
5.
The cesium fluoride (CsF)-assisted cross-coupling reaction of (1-fluorovinyl)methyldiphenylsilane (1) with aryl halides and aryl triflates was examined. The reaction with aryl iodides smoothly proceeded to afford the corresponding (1-fluorovinyl)arenes in the presence of a catalytic amount of CuI and Pd(PPh(3))(4) in aprotic polar solvents such as DMF, DMI, DMA, and NMP in good yields. A variety of functional groups (nitro, ester, ketone, and ether) on the aromatic rings can be tolerated under these mild conditions. Aryl iodides are superior to aryl bromides as the coupling reaction partner. The cross-coupling reaction of 1 with aryl triflates instead of aryl halides was also accomplished in the presence of tetrabutylammonium iodide (n-Bu(4)NI) as the additive under similar conditions. 相似文献
6.
Palladium‐catalysed reductive carbonylation of aryl halides with iron pentacarbonyl for synthesis of aromatic aldehydes and deuterated aldehydes
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Nasser Iranpoor Habib Firouzabadi Elham Etemadi‐Davan Abed Rostami Khashayar Rajabi Moghadam 《应用有机金属化学》2015,29(11):719-724
The first use of iron pentacarbonyl is described for the novel and efficient conversion of aryl iodides, bromides and chlorides into their corresponding aryl aldehydes and/or aryl deuterated aldehydes. The reaction is catalysed with Pd(0) in aqueous N,N‐dimethylformamide at atmospheric pressure. In this protocol, neither gaseous hydrogen nor any reducing agent is required for the formation of the carbonylated product. The reaction can be performed without a P(III) ligand for aryl iodides; however, employing a P(III) ligand is necessary to perform the reaction with aryl bromides and chlorides. Copyright © 2015 John Wiley & Sons, Ltd. 相似文献
7.
A rhodium complex catalyzed the reaction of aryl methyl ethers and thioesters giving the corresponding aryl esters and methyl sulfides. S-(p-Chlorophenyl) p-(dimethylamino)benzothioate was used for the reaction of methyl aryl ethers with electron-withdrawing groups, and an S-(p-tolyl) derivative was used for those with electron-donating groups. Polymethoxybenzenes were converted to the esters in a regioselective manner. 相似文献
8.
Paulose TA Wu SC Olson JA Chau T Theaker N Hassler M Quail JW Foley SR 《Dalton transactions (Cambridge, England : 2003)》2012,41(1):251-260
Air and moisture stable homoleptic bis(diimidazolylidine)nickel(II) complexes, ([(diNHC)(2)Ni](2+)) 3a,b and their corresponding silver(I) 4a,b and palladium(II) 5a,b complexes were synthesized and characterized by NMR and single crystal X-ray analysis. The catalytic potential of complex 3a was assessed in Mizoroki-Heck and Suzuki-Miyaura coupling reactions. In the Suzuki-Miyaura coupling reaction, nickel precatalyst 3a was active for the coupling of aryl chlorides as well as aryl fluorides. The analogously synthesized Pd(II) complexes resulted in formation of (diNHC)PdCl(2) species which were not active for the coupling of aryl fluorides. For the Mizoroki-Heck reaction, it was found that aryl iodides could be activated in the absence of nickel or palladium precatalysts when using Na(2)CO(3) or NEt(3) as base while aryl iodides and aryl bromides could be activated in the Suzuki-Miyaura reaction sans precatalyst when K(3)PO(4) was used as base. 相似文献
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11.
Manickam Bakthadoss Anthonisamy Devaraj Jayakumar Srinivasan 《Journal of heterocyclic chemistry》2015,52(2):418-424
In this article, a simple method for the synthesis of bis(di(indolyl)aryl)methanes is described. The iodine‐catalyzed (5 mol %) reaction of indoles with various bis(salicylaldehyde) derivatives affords the bis(di(indolyl)aryl)methanes in excellent yields. The reaction works well under mild reaction condition with shorter reaction time. 相似文献
12.
Heck reaction catalyzed by PD-modified zeolites. 总被引:2,自引:0,他引:2
[Pd]-exchanged NaY zeolites have been prepared, characterized, and applied for the first time for catalytic carbon-carbon coupling reactions. The catalysts exhibit a high activity and selectivity toward the Heck reaction of aryl bromides with olefins for small palladium concentrations (< or =0.1 mol % of Pd). The catalysts can easily be separated from the reaction mixture and reused after washing without loss in activity. No limitation to the diffusion of adducts in the zeolite cages was observed (for linear alkenes). The electronic nature of the aryl bromides and the olefins has a dominating effect on the reaction yield and selectivity. The heterogeneous catalysts quantitatively convert all types of all aryl bromide (complete conversion of bromobenzene within 30 min) and activated aryl chlorides under standard reaction conditions. Product form selectivity is observed in the Heck reaction with cyclic olefins. 相似文献
13.
Shekhar S Dunn TB Kotecki BJ Montavon DK Cullen SC 《The Journal of organic chemistry》2011,76(11):4552-4563
A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K(3)PO(4) in tert-amyl alcohol was found to be the optimal base-solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction. 相似文献
14.
Benjamin E. Fener Philipp Schüler Dr. Nico Ueberschaar Dr. Peter Bellstedt Dr. Helmar Görls Dr. Sven Krieck Prof. Dr. Matthias Westerhausen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(32):7235-7243
The hydrophosphorylation of phenylacetylene with di(aryl)phosphane oxides Ar2P(O)H (Pudovik reaction) yields E/Z-isomer mixtures of phenylethenyl-di(aryl)phosphane oxides ( 1 ). Alkali and alkaline-earth metal di(aryl)phosphinites have been studied as catalysts for this reaction with increasing activity for the heavier s-block metals. The Pudovik reaction can only be mediated for di(aryl)phosphane oxides whereas P-bound alkyl and alcoholate substituents impede the P−H addition across alkynes. The demanding mesityl group favors the single-hydrophosphorylated products 1-Ar whereas smaller aryl substituents lead to the double-hydrophosphorylated products 2-Ar . Polar solvents are beneficial for an effective addition. Increasing concentration of the reactants and the catalyst accelerates the Pudovik reaction. Whereas Mes2P(O)H does not form the bis-phosphorylated product 2-Mes , activation of an ortho-methyl group and cyclization occurs yielding 2-benzyl-1-mesityl-5,7-dimethyl-2,3-dihydrophosphindole 1-oxide ( 3 ). 相似文献
15.
The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the synthesis of aryl fluorides, however, are limited. We report the conversion of a diverse set of aryl iodides to the corresponding aryl fluorides. This reaction occurs with a cationic copper reagent and silver fluoride. Preliminary results suggest this reaction is enabled by a facile reductive elimination from a cationic arylcopper(III) fluoride. 相似文献
16.
Synthesis and characterization of monodisperse oligofluorenes 总被引:1,自引:0,他引:1
Jo J Chi C Höger S Wegner G Yoon DY 《Chemistry (Weinheim an der Bergstrasse, Germany)》2004,10(11):2681-2688
An efficient synthesis of 9,9-bis(2-ethylhexyl)fluorene oligomers up to the heptamer is reported, with repetitive Suzuki and Yamamoto coupling reactions employed in the synthesis. The key steps for preparation of the essential intermediates include Pd-catalyzed transformation of aryl bromides to aryl boronic esters (Miyaura reaction) and the application of the much higher reactivity of aryl boronic esters over aryl bromides in the Pd-catalyzed cross-coupling reaction with aryl diazonium salts. Variation of the UV/Vis absorption and photoluminescence characteristics with chain length is reported. Moreover, glass transition and liquid-crystal characteristics of the oligomers are described and compared with those of the polymer. 相似文献
17.
A convenient procedure for preparing some arylureas having herbicidal properties is reported. The method has two steps: (1) reaction of arylamine with chlorocarbonylsulfenyl chloride in the presence of nonpolar solvent to produce aryl carbonylsulfenyl chloride and (2) reaction with dimethylamine in a two-phase reaction catalysed by phase-transfer catalyst to produce the corresponding aryl ureas. 相似文献
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以氯代芳烃为底物,季鏻盐[PPh4]Br为助催化剂,用于环钯催化的Heek芳基化反应.结果表明,在环钯-[PPh4]Br催化体系中,以Na2CO3作为碱性试剂,使用0.3mol%Pd的环钯催化剂催化氯苯的Heek反应,就可得到比较高的产率(88%)和转化率(90%).对于大部分卤代芳烃Heck反应而言,环钯-[PPh4]Br是一种有效的催化体系,即使是对含推电子基团的不活泼的氯代芳烃,在此体系中也能获得比较好的结果.此外,文中还探讨了反应温度、[PPh4]Br/Pd比值及催化剂回用对反应活性的影响. 相似文献
20.
WU Qiang JIN Rizhe KANG Chuanqing CHEN Wenhui BIAN Zheng MA Xiaoye DING Jinying GUO Haiquan QIU Xuepeng GAO Lianxun 《高等学校化学研究》2016,32(1):55-61
This study details Ni-catalyzed cross coupling of aryl Grignard reagents with aryl halides in toluene, a nonpolar solvent with a high boiling point. The reaction was applied for the synthesis of various biaryls in good yields without the introduction of a large steric ligand. The Kumada-Tamao-Corriu(KTC) reaction in toluene was then successfully modified to proceed under neat conditions for the efficient syntheses of symmetrical biaryls, particularly in large-scale preparations. Unactivated aryl chlorides show higher reactivity than aryl bromides, particularly under neat conditions. Mechanistic investigations suggest a radical procedure for the catalytic cycle, and the origin of the radical intermediates being aryl halides. 相似文献