- Pd nanoparticles immobilized on poly(NIPAM-co-4-VP) hydrogel: Highly active and reusable catalyst for carbon-carbon coupling reactions in water
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Poly(N-isopropylacrylamide-co-4-vinylpyridine) [poly(NIPAM-co-4-VP)] co-polymer exhibited inverse temperature solubility with a lower critical solution temperature (LCST) in water. Pd nanoparticles were immobilized on these poly(NIPAM-co-4-VP) hydrogels. The heterogeneous Pd catalyst showed high catalytic activities for carbon-carbon coupling reactions, such as Suzuki-Miyaura, Heck-Mizoroki, and Sonogashira coupling reactions in water. The Pd catalyst immobilized on poly(NIPAM-co-4-VP) hydrogel (NIPAM:4-VP = 1:1 M ratio) showed an excellent recyclability and excellent yield for carbon-carbon coupling reactions.
- Lee, Yongwoo,Hong, Myeng Chan,Ahn, Hyunseok,Yu, Jeongmok,Rhee, Hakjune
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- Sonogashira cross-coupling of arenediazonium salts
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(Figure Presented) Star-crossed lovers: The domino iododediazoniation/ Sonogashira cross-coupling of terminal alkynes with arenediazonium salts has been developed. The arenediazonium salt synthesis/iododediazoniation/Sonogashira cross-coupling sequence can also be performed as a one-pot process, omitting the isolation of the arenediazonium salt.
- Fabrizi, Giancarlo,Goggiamani, Antonella,Sferrazza, Alessio,Cacchi, Sandro
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- Encapsulating palladium nanoparticles inside ethylenediamine functionalized and crosslinked chlorinated poly(vinyl chloride) nanofibers as an efficient and stable heterogeneous catalyst for coupling reactions
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Palladium chloride and chlorinated poly (vinyl chloride) (CPVC) mixture were prepared into homogeneous solution, followed by electrospinning to make uniform nanofibers with average diameter of ~460 nm. Then, these composite nanofibers were treated in ethy
- Du, Yijun,Qi, Chenze,Qin, Min,Shao, Linjun,Tao, Hongyu,Wang, Qingqing
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- (BeDABCO)2Pd2Cl6 as an efficient homogeneous catalyst for copper-free Sonogashira cross-coupling reaction
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An efficient catalytic system using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2] octane chloride and palladium chloride ((BeDABCO)2Pd 2Cl6) was developed for the Sonogashira reaction. In the presence of a catalytic amount of this efficient, stable homogeneous catalytic system that is non-sensitive to air and moisture, various aryl halides were efficiently coupled with phenylacetylene in good yields in H2O at 50C under copper-free conditions. Benzyl dabco as an efficient ligand and also a quaternary ammonium salt had an efficient stabilizing effect on the Pd(0) species. Copyright
- Hajipour, Abdol R.,Rafiee, Fatemeh
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- The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder
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The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder has been developed; terminal alkynes couple with aryl, alkenyl iodide and aryl bromide in the presence of cuprous iodide, triphenylphosphine, potassium hydroxide and ultrafine particle nickel(0) to provide the corresponding cross-coupling products with high yields.
- Wang, Lei,Li, Pinhua,Zhang, Yicheng
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- Tandem Sonogashira coupling: An efficient tool for the synthesis of diarylalkynes
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(Chemical Equation Presented) The tandem Sonogashira coupling reaction of aryl halides provides an efficient method for the synthesis of diarylalkynes. Several aryl halides were coupled with 2-methyl-3-butyn-2-ol as acetylene source in the presence of PdCl2(PPh3)2 and CuI. Following the deprotection of the acetylene moiety in the same pot using a strong base, the Sonogashira coupling of a second aryl halide led to the formation of the appropriate diarylakyne. The established protocoll was successfully extended to the preparation of compound libraries.
- Novak, Zoltan,Nemes, Peter,Kotschy, Andras
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- DBU-Mediated Efficient Synthesis of Diaryl Ethynes and Enynes from 1,1-Dibromoalkenes at Room Temperature
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The reaction of 1,1-dibromoalkenes and aryl iodides in the presence of DBU and a PdII/CuI catalytic system afforded diaryl alkynes and enynes at ambient temperature. Control experiments demonstrated the essential ligand role of DBU i
- Thummala, Yadagiri,Morri, Ashok K.,Karunakar, Galla V.,Doddi, Venkata Ramana
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- Synthesis of Internal Alkynes through an Effective Tandem Elimination-Hydrodebromination-Cross-Coupling of gem-Dibromoalkenes with Halobenzenes
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Carbon-carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C-C cross-coupling reaction of two kinds of organic halide, a gem -dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination-hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.
- Ji, Yuan,Zhong, Ning,Kang, Zinan,Yan, Guobing,Zhao, Ming
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- Copper- and phosphine-free Sonogashira coupling reaction catalyzed by silica-(acac)-supported palladium nanoparticles in water
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A palladium-based catalyst supported on acac-functionalized silica was used as a heterogeneous catalyst for the Sonogashira cross-coupling reaction of various aryl halides and phenylacetylene under copper- and phosphine-free conditions. This catalytic sys
- Hajipour, Abdol R.,Shirdashtzade, Zohre,Azizi, Ghobad
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- Visible light-mediated gold-catalysed carbon(sp2)-carbon(sp) cross-coupling
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A dual photoredox and gold-catalysed cross-coupling reaction of alkynyltrimethylsilanes and aryldiazonium tetrafluoroborates is described. The reaction proceeds through visible-light mediated oxidative addition of aryldiazoniums, transmetalation of alkynyltrimethylsilanes and aryl-alkynyl reductive elimination. Exclusive selectivity for silyl-substituted alkynes is observed, with no reactivity observed for terminal alkynes.
- Kim, Suhong,Rojas-Martin, Jaime,Toste, F. Dean
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- Palladium-catalyzed Reaction of Phenyl Fluoroalkanesulfonates with Alkynes and Alkenes
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Palladium-catalyzed reaction of phenyl fluoroalkanesulfonates with alkynes and alkens under mild conditions gives the corresponding alkynyl and alkenyl substituted benzenes in good yields.
- Chen, Qing-Yun,Yang, Zhen-Yu
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- Efficient Sonogashira and Suzuki-Miyaura coupling reaction catalyzed by Pd-Nanoparticles
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The Pd nano particles were electrochemically deposited on nafion-graphene. They showed excellent catalytic activity towards Sonogashira and Suzuki-Miyaura cross-coupling reaction. Benzenediazonium salts were used as alternative to aromatic halide. The developed protocol offers recyclability, easy workups with short reaction time and good-to-excellent product yield. [Figure not available: see fulltext.]
- Balsane, Kishor E.,Shendage, Suresh S.,Nagarkar, Jayashree M.
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- Microwave-assisted Sonogashira cross-coupling reaction catalyzed by CN-ortho-palladated complex of tribenzylamine under copper-free conditions
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Abstract The catalytic activity of [Pd{C6H4(CH2N(CH2Ph)2)} (μ-Br)]2 complex as an efficient, stable and non-sensitive to air and moisture catalyst was investigated in the Sonogashira cross-coupling reaction under microwave irradiation. In the presence of catalytic amount of this homogeneous catalytic system, various aryl halides were efficiently coupled with phenylacetylene under copper-free conditions. The substituted internal alkynes were produced in excellent yields in short reaction times in NMP at 100°. The combination of dimeric complex as homogenous catalyst and microwave irradiation and also NMP as microwave-active polar solvent gave higher yields in shorter reaction times.
- Hajipour, Abdol R.,Rafiee, Fatemeh
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- A simple and greener approach for the synthesis of PVC supported Pd (0): Application to Heck and Sonogashira reactions in water
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Preparation of PVC-supported Pd nanoparticles through the reduction of PdCl2 by a non-toxic and eco-friendly route, employing sodium formate and NaOH in ethanol-water system has been described. The prepared PVC supported Pd nanoparticles were employed as catalyst in the cross coupling reactions, that is, Heck and Sonogashira reactions in water medium to afford the respective products in good to excellent yields.
- Basavaprabhu,Samarasimhareddy,Prabhu, Girish,Sureshbabu, Vommina V.
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- Pd(NHC)PEPPSI-diazonium salts: An efficient blend for the decarboxylative Sonogashira cross coupling reaction
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An efficient N-heterocyclic carbene based Pd complex is described for the de-carboxylative Sonogashira coupling reaction with diazonium salts under ligand and co-catalyst free conditions. Pd(NHC)PEPPSI not only offers an air and moisture stable pre-cataly
- Bhojane, Jeevan Manohar,Jadhav, Vilas Gangadhar,Nagarkar, Jayashree Milind
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- Functionalized α,β-ynones: Efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction
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Under the classic reaction conditions, a large excess of copper catalyst and N, O donor ligands were mandatory for the catalytic cross-coupling of Csp2-Csp bonds. Herein, we wish to report α,β-ynones as σ-, π-electron donating ligands for copper catalyzed Sonogashira-type reaction. As low as 0.25-2.5 mol% of L11 (3-(4-bromophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-one) significantly accelerated the 0.1-1.0 mol% of CuI catalyzed cross-coupling of aryl iodides with terminal alkynes and alkynylcarboxylic acids, respectively. This low-mol% catalyst system showed satisfactory activity and tolerance with 36 examples of substituted alkynes.
- Wang, Xian,Wang, Zhenhua,Xie, Zunyuan,Zhang, Guofang,Zhang, Weiqiang,Gao, Ziwei
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p. 109296 - 109300
(2016)
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- Palladium nanoparticles embedded in improved mesoporous silica: A pH-triggered phase transfer catalyst for Sonogashira reaction
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An efficient and reusable pH-responsive mesoporous silica nanocomposite shuttle-supported palladium catalyst was synthesized, which efficiently promotes the Sonogashira reaction in water-based biphasic systems. This catalyst of shell-embedded palladium nanoparticles is highly dispersed in organic phase in a pH range from 9 to 10 just like a homogeneous catalyst, and can be separated and reused like a heterogeneous one by adjusting the pH value of the aqueous medium. In addition, Sonogashira reactions can be performed without a copper co-catalyst.
- Zhao, Xiaohua,Liu, Xiang,Zhu, Yaoqin,Lu, Ming
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- Three-component indole synthesis using ortho-dihaloarenes
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A three-component synthesis of substituted indoles is accomplished starting from ortho-dihaloarenes through the use of a multicatalytic system consisting of an N-heterocyclic carbene palladium complex and CuI. The corresponding indole derivatives are obtained as single regioisomers in high yields of isolated product.
- Kaspar, Ludwig T.,Ackermann, Lutz
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- Dimeric ortho-palladated homoveratrylamine as an efficient homogeneous catalyst for copper-free Sonogashira cross-coupling reaction
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The catalytic activity of ortho-palladated [Pd{C6H2(CH2CH2NH2)-(OMe)2,3,4} (m-Br)]2, a complex of homoveratrylamine in the copper-free Sonogashira coupling reaction has been investigated. This complex is a catalyst that is efficient, stable and non-sensitive to air and moisture in the Sonogashira reaction. In this homogeneous catalytic system, various aryl halides were efficiently coupled with phenylacetylene in mostly moderate to good yields in N-methylpyrrolidone at 100 °C under copper-free conditions. Copyright
- Hajipour, Abdol R.,Rahimi, Hannaneh,Rafiee, Fatemeh
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- Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide
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Arylsulfonyl hydrazides were employed as coupling partners for the decarboxylative coupling reaction of propiolic acid derivatives. When the reaction was conducted using Pd(TFA) 2 (1.0 mol%), dppp (1.0 mol%), and Cu(OAc) 2 (2.4 equiv
- Park, Jaerim,Song, Kwang Ho,Lee, Sunwoo
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- Manganese-catalyzed Sonogashira coupling of aryl iodides
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An interesting manganese-catalyzed Sonogashira coupling reaction of aryl iodides has been developed. With PEG-400 as the green solvent and under mild reaction conditions, a variety of diarylacetylenes were obtained in moderate to good yields.
- Qi, Xinxin,Jiang, Li-Bing,Wu, Xiao-Feng
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- Synthesis and characterization of Fe3O4@SiO 2-polymer-imid-Pd magnetic porous nanospheres and their application as a novel recyclable catalyst for Sonogashira-Hagihara coupling reactions
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We demonstrate herein the modification of magnetic nanoparticles and their use as a magnetic nanocatalyst in direct coupling reactions of aryl halides with terminal alkynes. Magnetite particles were prepared by simple co-precipitation method in aqueous me
- Mohsen, Esmaeilpour,Jaber, Javidi,Mehdi, Mokhtari Abarghoui,Fatemeh, Nowroozi Dodeji
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- A novel indium-catalyzed sonogashira coupling reaction, effected in the absence of a copper salt, phosphine ligand and palladium
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An efficient copper-, phosphine ligand- and palladium-free indium-catalyzed Sonogashira coupling reaction has been developed in the presence of 1 mol% indium trichloride. Coupling of various aryl halides with terminal alkynes afforded the corresponding aryl alkynes in moderate to excellent yields. Georg Thieme Verlag Stuttgart.
- Borah, Harsha N.,Prajapati, Dipak,Boruah, Ramesh C.
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- Facile one-pot synthesis of diarylacetylenes from arylaldehydes: Via an addition-double elimination process
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A practical one-pot protocol has been developed to synthesize diarylacetylenes from arylaldehydes by treatment with 1-(arylmethyl)benzotriazoles and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of 1-bromo-4-(phenylethynyl)benzene has been demonstrated.
- Chen, Jianyang,Zhang, Xuan,Wu, Jiajun,Wang, Rui,Lei, Chunlin,An, Yanan
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p. 4701 - 4705
(2021/06/11)
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- Copper(0) nanoparticle catalyzed Z-Selective Transfer Semihydrogenation of Internal Alkynes
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The use of copper(0) nanoparticles in the transfer semihydrogenation of alkynes has been investigated as a lead-free alternative to Lindlar catalysts. A stereo-selective methodology for the hydrogenation of internal alkynes to the corresponding (Z)-alkenes in high isolated yields (86% average) has been developed. This green and sustainable transfer hydrogenation protocol relies on non-noble copper nanoparticles for reduction of both electron-rich and electron-deficient, aliphatic-substituted and aromatic- substituted internal alkynes. Polyols, such as ethylene glycol and glycerol, have been proven to act as hydrogen sources, and excellent stereo- and chemoselectivity have been observed. Enabling technologies, such as microwave and ultrasound irradiation are shown to enhance heat and mass transfer, whether used alone or in combination, resulting in a decrease in reaction time from hours to minutes. (Figure presented.).
- Moran, Maria Jesus,Martina, Katia,Bieliunas, Vidmantas,Baricco, Francesca,Tagliapietra, Silvia,Berlier, Gloria,De Borggraeve, Wim M.,Cravotto, Giancarlo
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supporting information
p. 2850 - 2860
(2021/05/06)
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- Simple and efficient diaryl alkyne synthesis method
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The embodiment of the invention discloses a simple and efficient diaryl alkyne synthesis method. The method comprises the steps of by taking arylmethylbenzotriazole and aromatic aldehyde as raw materials, carrying out addition and double-beta-elimination reaction under the action of bis (trimethylsilyl) amino salt MN (SiMe3) 2 to synthesize diaryl alkyne by a one-pot method. The raw materials and chemical reagents used in the method are easy to obtain, the reaction conditions are mild, the operation is simple, the substrate universality is good, the product yield is high, and the method is a simple and efficient diaryl alkyne synthesis method.
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Paragraph 0026; 0029-0031
(2021/04/14)
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- Visible Light-Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis
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A convenient method mediated by photoredox catalysis is developed for the direct construction of aryl alkynes. Readily available aromatic diazonium salts have been utilized as the aryl radical source to couple alkynyl carboxylic acids to feature the decarboxylative arylation. A wide range of substrates are amenable to this protocol with broad functional group tolerance, and diversely-functionalized aryl alkynes could be synthesized under mild, neutral and transition metal-free reaction conditions using visible light irradiation. Alongside synthetic sustainability associated with the photocatalytic and transition metal-free operation, another key point of this method is that the organic dye catalyst acts as an excited-state reductant, thus establishing the quenching cycle for radical addition and decarboxylative elimination. (Figure presented.).
- Yang, Liangfeng,Li, Haifeng,Du, Yijun,Cheng, Kai,Qi, Chenze
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p. 5030 - 5041
(2019/11/03)
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- Preparation method of aryl alkyne catalyzed by visible light
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The invention discloses a simple and convenient method for directly synthesizing an aryl alkyne compound through photoredox catalysis. Aryl fluoroborate diazoate is used as an aryl free radical source, and different types of aryl alkyne are synthesized in situ through a decarboxylation process. A reaction has good functional group tolerability, and a simple domestic visible light source can be used for synthesizing the aryl alkyne of different functional groups under mild, neutral and transition-free metal reaction conditions.
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Paragraph 0050-0053
(2019/11/13)
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- A palladium catalyzed aryl alkyne preparation method
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The invention discloses a palladium catalyzed aryl alkyne of the preparation method, comprises the following steps: in the catalyst, under the action of the ligand and alkali, substituted with aryl sulfonyl chloride alkynoic occurs in the organic solvent escapes suosuo the coupling reaction, after the reaction is finished after treatment to obtain the aryl alkyne. Used in the preparation method of the cheap raw material, the reaction and simple post treatment operation, at the same time, the reaction less side reaction, high yield of the product.
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Paragraph 0037; 0038; 0039
(2019/05/21)
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- Arylation of Terminal Alkynes by Aryl Iodides Catalyzed by a Parts-per-Million Loading of Palladium Acetate
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Arylation of terminal alkynes (16 varieties) by aryl iodides (28 varieties) was achieved with a mol ppm loading level of palladium catalyst, where a variety of functional groups including heteroarenes were tolerated. Thus, the arylations were carried out in the presence of palladium acetate at ppm loadings and potassium carbonate in ethanol at 80 °C to give the corresponding internal alkynes in good to excellent yields. Synthesis of 2-phenyl-3-(phenylalkynyl)benzofuran was achieved by iterative use of the alkyne arylation under mol ppm catalytic conditions. Reaction-rate analysis, transmission electron microscopic (TEM) examination of the reaction mixture, and mercury-amalgamation test were performed to gain insight into the active species of the highly active ppm catalytic species. TEM examination of the reaction mixture revealed that palladium nanoparticles were generated in situ under the reaction conditions, and their cluster size was variable during the catalytic reaction. A variation in size of palladium particles suggested that the composition-decomposition process of Pd aggregates should take place in situ via monomeric palladium(0) species and/or fine palladium(0) clusters, which might be real catalytic species in this reaction.
- Hamasaka, Go,Roy, David,Tazawa, Aya,Uozumi, Yasuhiro
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p. 11640 - 11646
(2019/12/02)
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- SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes
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Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).
- Zha, Gao-Feng,Fang, Wan-Yin,Li, You-Gui,Leng, Jing,Chen, Xing,Qin, Hua-Li
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p. 17666 - 17673
(2019/01/04)
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- Dimethylisosorbide (DMI) as a Bio-Derived Solvent for Pd-Catalyzed Cross-Coupling Reactions
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Palladium-catalyzed bond-forming reactions, such as the ?-Suzuki-Miyaura and Mizoroki-Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalyzed reactions: Suzuki-Miyaura (13 examples, 62-100% yield), Mizoroki-Heck (13 examples, 47-91% yield), and Sonogashira (12 examples, 65-98% yield).
- Wilson, Kirsty L.,Murray, Jane,Sneddon, Helen F.,Jamieson, Craig,Watson, Allan J. B.
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supporting information
p. 2293 - 2297
(2018/10/20)
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- Sonogashira-type cross-coupling reactions catalyzed by copper complexes of pincer N-heterocyclic carbenes
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Copper complexes of N-heterocyclic carbenes (NHC) have recently received great attention in catalysis, however, the application scope has been limited to neutral complexes bearing monodentate ligands. Herein, we report the synthesis and full characterization of a cationic Cu-pincer bis(NHC) complex with bulky tert-butyl wingtips that serves as catalyst for the coupling of aryl iodides and phenylacetylene, alongside its analogs with small alkyl substituents. Unlike other copper catalysts that require an inert atmosphere to prevent alkyne homocoupling, a competing side reaction to Sonogashira reaction, the Cu-pincer bis(NHC) complexes provide good to excellent cross-coupling yields in air. Interestingly, the reaction under argon affords substantially reduced cross-coupling, indicative of the oxygen involvement and its facilitating effect in the mechanism. In our controlled studies, the air-assisted cross-coupling reaction came to a complete stop when using a radical trap, suggesting the presence of a radical in the mechanism. Examining the reaction of Cu-pincer bis(NHC) complexes with oxygen via UV–vis spectroscopy reveals a dark green chromophore formation at ?40 °C with strong absorbance (ε > 400 M?1cm?1) at 460 nm and 500 nm, likely due to a high-valent copper-oxygen adduct.
- Domyati, Doaa,Latifi, Reza,Tahsini, Laleh
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supporting information
p. 98 - 105
(2018/03/06)
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- Further insight into the photochemical behavior of 3-aryl-N-(arylsulfonyl)propiolamides: tunable synthetic route to phenanthrenes
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Reported herein is further insight into the photochemical behaviour of 3-aryl-N-(arylsulfonyl)-propiolamides, which provides a straightforward way to access meaningful phenanthrenes. Mechanistic investigation indicated that aryl migration, C-C coupling, 1,3-hydrogen shift, desulfonylation and elimination were involved in the process. Moreover, this protocol allowed for scale-up using a flow reactor.
- Chen, Ming,Zhao, Xinxin,Yang, Chao,Wang, Yanpei,Xia, Wujiong
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p. 12022 - 12026
(2017/03/01)
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- Method for synthesizing multi-substituted alkyne
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The invention discloses a method for synthesizing multi-substituted alkyne, relates to the technical field of synthesis of multi-substituted alkyne and provides a method for synthesizing multi-substituted alkyne through terminal alkyne and halide of sp2 type carbon under the catalysis of a polyaniline supported nano-palladium catalyst. According to the method, polyaniline supported nano-palladium is taken as a catalyst, diisopropyl-2-ethyoxyl ethylamine is taken as alkali, and multi-substituted alkyne is directly synthesized in one step through cross coupling. Compared with conventional methods, the method has the advantages that raw materials are simple and easy to obtain, the cost is low, the catalyst is mild, environment-friendly and rich, and a solvent is clean and environment-friendly. Thus, a clean and practical synthesis method is provided for synthesis of such important compounds.
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Paragraph 0012; 0013; 0022; 0023
(2016/11/24)
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- Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation
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Pd-catalysed C-C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (Cyrene) in Sonogashira cross-coupling and Cacchi-type annulations.
- Wilson, Kirsty L.,Kennedy, Alan R.,Murray, Jane,Greatrex, Ben,Jamieson, Craig,Watson, Allan J. B.
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supporting information
p. 2005 - 2011
(2016/10/05)
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- Novel chitosan-based/montmorillonite/palladium hybrid microspheres as heterogeneous catalyst for Sonogashira reactions
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The objective of this study was to develop novel chitosan-based/montmorillonite/palladium (CS/MMT/Pd) hybrid microsphere catalysts with improved properties for use in Sonogashira reactions. Interactions between a chitosan matrix and a montmorillonite nano
- Zeng, Minfeng,Yuan, Xia,Zuo, Shufeng,Qi, Chenze
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p. 37995 - 38000
(2015/07/27)
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- Pd-tetrahydrosalan-type complexes as catalysts for sonogashira couplings in water: Efficient greening of the procedure
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New sulfonated tetrahydrosalen-type ligands and their water-soluble palladium(II) complexes have been synthesized. The palladium(II) complexes catalyze the Sonogashira coupling (23 examples) of various aryl halides (including chloroarenes) with terminal alkynes, with good to excellent conversions under mild conditions (80 °C, air, no CuI cocatalyst) in aqueous-organic mixtures and turnover frequencies of up to 2790 h -1. Under optimized reaction conditions to minimize environmental contamination, diphenylacetylenes can be isolated in 76-98 % yield. The aqueous catalyst solution can be recycled four times with decreasing activity; however, yields between 93 and 98 % can still be achieved with extended reaction times. Several water-insoluble products can be isolated in excellent yield by simple filtration and purification by washing with water; this method is used, for the first time, for this type of C - C coupling procedure.
- Voronova, Krisztina,Homolya, Levente,Udvardy, Antal,Benyei, Attila C.,Joo, Ferenc
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p. 2230 - 2239
(2014/10/15)
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- Flow-based, cerium oxide enhanced, low-level palladium sonogashira and heck coupling reactions by perovskite catalysts
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A flow chemistry procedure for Sonogashira and Heck cross-coupling reactions using a low-level palladium perovskite catalyst (LaFe 0.95Pd0.05O3) deposited on cerium oxide is reported. The catalyst was generated in situ at
- Battilocchio, Claudio,Bhawal, Benjamin N.,Chorghade, Rajeev,Deadman, Benjamin J.,Hawkins, Joel M.,Ley, Steven V.
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p. 371 - 380
(2014/05/06)
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- Stereoselective iron-catalyzed alkyne hydrogenation in ionic liquids
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Iron(0) nanoparticles in ionic liquids (ILs) have been shown to catalyse the semi-hydrogenation of alkynes. In the presence of a nitrile-functionalised IL or acetonitrile, stereoselective formation of (Z)-alkenes was observed. The biphasic solvent system allowed facile separation and re-use of the catalyst. The Royal Society of Chemistry 2014.
- Gieshoff, Tim N.,Welther, Alice,Kessler, Michael T.,Prechtl, Martin H.G.,Jacobi Von Wangelin, Axel
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supporting information
p. 2261 - 2264
(2014/03/21)
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- An efficient protocol for copper-free palladium-catalyzed Sonogashira cross-coupling in aqueous media at low temperatures
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A thorough study on copper-free Sonogashira cross-couplings in water was carried out using the palla-dacycle, [{Pd(μ-Cl){K2-P,C-P(iPr) 2(OC6H3-2-Ph)}}2] as pre-catalyst with different bases and palladium concentrations. The highly active pre-catalyst imparts good to near quantitative yields using a concentration of 0.25 mol % at 40 °C. This broadly applicable protocol exhibits high tolerance of functional groups and substitution patterns.
- Marziale, Alexander N.,Schlüter, Johannes,Eppinger, J?rg
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supporting information; experimental part
p. 6355 - 6358
(2011/12/22)
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- Continuous flow coupling and decarboxylation reactions promoted by copper tubing
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A convenient and efficient flow method for Ullmann condensations, Sonogashira couplings, and decarboxylation reactions using a commercially available copper tube flow reactor (CTFR) is described. The heated CTFR effects these transformations without added metals (e.g., Pd), ligands, or reagents, and in greater than 90% yield in most cases examined.
- Zhang, Yun,Jamison, Timothy F.,Patel, Sejal,Mainolfi, Nello
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supporting information; experimental part
p. 280 - 283
(2011/04/15)
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- A general and mild domino approach to substituted 1-aminoindoles
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A versatile and efficient palladium catalyzed domino reaction leading to a broad range of substituted 1-aminoindoles has been developed. The title compounds were prepared from 2-halo-phenylacetylenes and simple hydrazines in good to excellent yields in ju
- Halland, Nis,Nazare, Marc,Alonso, Jorge,R'Kyek, Omar,Lindenschmidt, Andreas
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supporting information; experimental part
p. 1042 - 1044
(2011/02/27)
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- Copper-Free Sonogashira coupling in water with an amphiphilic resin-supported palladium complex
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The palladium-catalyzed coupling reaction of aryl halides with terminal alkynes, the Sonogashira coupling, took place in water under copper-free conditions by use of an amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin-supported palladium-phosphine complex to give the corresponding aryl-substituted alkynes in high yields. The PS-PEG resin-supported palladium catalyst was recovered by simple filtration and reused four times without any loss of catalytic activity.
- Suzuka, Toshimasa,Okada, Yukari,Ooshiro, Kazumasa,Uozumi, Yasuhiro
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experimental part
p. 1064 - 1069
(2010/03/25)
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- A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH ARYL TOSYLATES
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The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-c
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Page/Page column 39
(2009/03/07)
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- Ethynyl-cyclohexanol: an efficient acetylene surrogate in Sonogashira coupling
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The Sonogashira coupling of aryl halides in the presence of 1-ethynyl-cyclohexanol as an acetylene source provides an efficient method for the synthesis of diarylacetylenes without the isolation of the appropriate arylacetylenes.
- Csékei, Márton,Novák, Zoltán,Kotschy, András
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p. 975 - 982
(2008/09/17)
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- Syntheses of substituted 3-methyleneisoindolin-1-ones by a palladium-catalyzed sonogashira coupling-carbonylation-hydroamination sequence in phosphonium salt-based ionic liquids
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(Chemical Equation Presented) Two efficient approaches for the synthesis of isoindolin-1-one derivatives in phosphonium salt ionic liquids are described. The palladium-catalyzed carbonylation-hydroamination reaction of 1-halo-2-alkynylbenzene with amines
- Cao, Hong,McNamee, Laura,Alper, Howard
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supporting information; experimental part
p. 5281 - 5284
(2009/06/18)
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- Sonogashira reaction of aryl halides with terminal alkynes catalyzed by cobalt hollow nanospheres
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Sonogashira reaction catalyzed by cobalt hollow nanospheres has been developed. Coupling of alkynes with aryl iodide or aryl bromide in the presence of potassium carbonate, triphenylphosphine, and cuprous iodide provides the corresponding products with mo
- Feng, Lizhe,Liu, Fangxian,Sun, Peipei,Bao, Jianchun
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experimental part
p. 1415 - 1417
(2009/04/06)
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- Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions
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A catalyst for the intramolecular direct arylation of a broad range of simple and heterocyclic arenes with aryl iodides, bromides, and chlorides has been developed. These reactions occur in excellent yield and are highly selective. Studies with aryl iodides substrates revealed that catalyst poisoning occurs due to the accumulation of iodide in the reaction media. This can be overcome by the addition of silver salts which also permits these reactions to occur at lower temperature. The utility of the methodology is illustrated by a rapid synthesis of a carbazole natural product and by the synthesis of sterically encumbered tetra-ortho-substituted biaryls via ring-opening reactions of the direct arylation products. Mechanistic investigations have provided insight into the catalyst's mode of action and show the presence of a kinetically significant C-H bond cleavage in palladium-catalyzed direct arylation of simple arenes. Knowledge garnered from these studies has led to the development of new intermolecular arylation reactions with previously inaccessible arenes, opening the door for the development of other new direct arylation processes.
- Campeau, Louis-Charles,Parisien, Mathieu,Jean, Annie,Fagnou, Keith
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p. 581 - 590
(2007/10/03)
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- Investigations into the Pd-catalysed cross-coupling of phenylacetylene with aryl chlorides: Simple one-pot procedure and the effect of ZnCl2 co-catalysis
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[PdCl{C6H3(OPPri2)2 -2,6}] 1 catalyses the coupling of electron-rich, electron-neutral and electron-deficient aryl chlorides with phenylacetylene in the presence of ZnCl2 as co-catalyst to
- Eberhard, Michael R.,Wang, Zhaohui,Jensen, Craig M.
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p. 818 - 819
(2007/10/03)
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