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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.
An efficient copper-catalyzed cross-coupling of aryl iodides with aryl acetylenes under microwave irradiation is described. The reaction proceeds under microwave heating with 10 mol % CuI and 2 equiv Cs2CO3 in 43-87% yields. 相似文献
3.
Cristau HJ Ouali A Spindler JF Taillefer M 《Chemistry (Weinheim an der Bergstrasse, Germany)》2005,11(8):2483-2492
An efficient copper-catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen- and/or oxygen-binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper-catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110 degrees C) compared with the Rosenmund-von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper-mediated cyanation reactions. 相似文献
4.
We present here an easy, rapid copper-free methodology for the Sonogashira coupling reaction. It works well for a range of aryl iodides and activated aryl bromides. 相似文献
5.
The catalytic activity of dimeric [Pd{C6H2(CH2CH2NH2)–(OMe)2,2,3}(m-Br)]2 complex was investigated in the synthesis of benzonitriles under microwave irradiation conditions. The substituted benzonitriles were produced from various aryl halides in excellent yields and short reaction times using a catalytic amount of this complex as efficient, stable and air- and moisture-tolerant catalyst, and K4[Fe(CN)6] as a green cyanide source in DMF at 130 °C. 相似文献
6.
Huan HeYong-Jin Wu 《Tetrahedron letters》2003,44(16):3385-3386
The copper-catalyzed N-arylation of sulfonamides with a variety of aryl bromides and iodides using microwave heating is described. 相似文献
7.
An efficient copper-mediated synthesis of aryl nitriles from aryl boronic acids has been achieved using benzyl cyanide as a user-friendly cyanide source. Various aryl boronic acids underwent the reaction smoothly, affording the corresponding aryl nitriles in moderate to good yields. tert-Butyl hydroperoxide (TBHP) was found to be a critical agent facilitating the cyanation reaction. 相似文献
8.
An efficient palladium catalytic system for microwave assisted cyanation of aryl halides 总被引:1,自引:0,他引:1
Abdol R. Hajipour Kazem Karami Azade Pirisedigh 《Journal of organometallic chemistry》2011,696(4):819-824
Application of a new catalytic system for cyanation reaction of various aryl halides using K4[Fe(CN)6] as cyanating source was examined. The reactions were performed under microwave irradiation and results showed that application of this catalytic system and DMF at 130 °C minimized the reaction times from hours to minutes in good to excellent yields. 相似文献
9.
Bahman Tamami Molki Mohaghegh Nezhad Soheila Ghasemi Fatemeh Farjadian 《Phosphorus, sulfur, and silicon and the related elements》2016,191(1):123-128
A new tridentate PCP pincer palladium (Pd) complex based on cross-linked Merrifield resin containing phosphinite ligand was synthesized and characterized. This polymeric catalyst was used in preparation of benzonitriles from different aryl iodides using potassium hexacyanoferrate (II) as a cyanide source. The presence of active metallic Pd in the catalyst was verified by X-ray power diffraction and X-ray photoelectron spectroscopy techniques. Transmission electron microscopy showed good dispersion of catalytic sites in the range of 30–50 nm. The catalyst is easily separated from reaction mixture and can be used for several times in repeating cycles without considerable loss of activity. The leaching of Pd from the support is negligible, which was confirmed by inductively coupled plasma–optical emission spectrometry and hot filtration test. 相似文献
10.
The microwave-promoted alkoxycarbonylation of aryl iodides using reaction vessels pre-pressurized with carbon monoxide is reported. Reactions are performed using 0.1 mol% palladium acetate as catalyst, DBU as base and are complete within 20-30 min. A range of aryl iodide substrates can be converted to the corresponding esters using this methodology. Primary and secondary alcohols work well whereas a tertiary alcohol substrate proves less reactive. The potential for scale-up of the reaction has also been explored. 相似文献
11.
Aminocarbonylation of aromatic iodides using aqueous ammonia in toluene has been developed. Various primary aromatic amides have been efficiently synthesized in good to excellent yields in the presence of catalytic quantities of Pd(OAc)2/CYTOP®292. The usage of aqueous ammonia avoids the handling of two gases in the reaction. 相似文献
12.
[reaction: see text] A practical, ligand-free cyanation of aryl bromides that utilizes as little as 0.1 mol % Pd(OAc)(2) in combination with a nontoxic cyanide source, M(4)[Fe(CN)(6)] (M = K, Na), is described. The reactions are performed in DMAC at 120 degrees C and provide the corresponding aryl nitrile in 83-96% yield, typically in less than 5 h. TON values of up to 7100 were attained. 相似文献
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15.
The use of catalytic t-Bu-P4 base dramatically improved the performance of halogen-zinc exchange of aryl iodides, and the arylzinc derivatives were functionalized under copper-free reaction conditions. 相似文献
16.
Takashi Mino Hiroaki Shindo Tomoko Kaneda Tomoko Koizumi Yoshio Kasashima Masami Sakamoto Tsutomu Fujita 《Tetrahedron letters》2009,50(38):5358-432
Palladium-catalyzed Mizoroki-Heck reaction of allyl aryl ethers with aryl iodides gave aryl cinnamyl ethers using a catalytic amount of Pd(OAc)2 in DMF at 50 °C with phosphine-free hydrazone as a ligand in good yields. 相似文献
17.
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
18.
Sundermeier M Zapf A Mutyala S Baumann W Sans J Weiss S Beller M 《Chemistry (Weinheim an der Bergstrasse, Germany)》2003,9(8):1828-1836
The development of new palladium catalysts for the cyanation of various aryl and heteroaryl chlorides is described. The combination of amine co-catalysts with chelating phosphine ligands, for example, 1,4-bis(diphenylphosphino)butane (dppb) or 1,5-bis(diphenylphosphino)pentane (dpppe), allows an efficient cyanation of chloroarenes with simple potassium cyanide. General palladium-catalyzed cyanation of nonactivated and deactivated chloroarenes is possible for the first time. Studies of the oxidative addition of aryl halides to palladium triphenylphosphine complexes in the presence and absence of amines suggest that the co-catalyst is capable of preventing catalyst deactivation caused by the presence of excess cyanide ions in solution. 相似文献
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20.
Guozhen He Yuan Huang Yao Tong Jie Zhang Dan Zhao Shuangli Zhou Shiqing Han 《Tetrahedron letters》2013
A green and efficient method has been developed for the cross-coupling of 2-mercaptobenzothiazoles with aryl iodides in water. The reactions proceeded smoothly under ligand-free conditions in the presence of TBAB to give the corresponding products in good yields. The protocol showed good tolerance toward a variety of functional groups. A substrate-promoted mechanism for this catalytic reaction has been proposed. 相似文献