- Immobilization of Pd catalysts on mesoporous silica for amine- and copper-free Sonogashira coupling reactions
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Immobilization of catalysts on solid supports is a promising approach to combine the advantages of heterogeneous and homogeneous catalysts. Pd(PPh3)2Cl2, known as an extremely active homogeneous catalyst for the Sonogashira coupling reaction, has been immobilized on high-surface-area MCF (mesocellular foams)-type mesoporous silica powder modified with 3-aminopropyltriethoxysilane and subsequently with diphenylphosphine. The functionalized MCF-type silica and supported catalysts have been characterized by x-ray photoelectron spectroscopy (XPS), fourier transform infrared spectroscopy (FTIR), elemental analysis, nitrogen sorption porosimetry, and scanning electron microscopy (SEM). Such supported Pd catalysts have proven to be useful recyclable reagents for copper- and amine-free Sonogashira coupling reactions of haloaromatic compounds with terminal alkynes. Copyright Taylor & Francis Group, LLC.
- Sotiriou-Leventis, Chariklia,Wang, Xiaojiang,Mulik, Sudhir,Thangavel, Arumugam,Leventis, Nicholas
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- Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation to Achieve Isoquinoline Synthesis
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We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.
- Cui, Hong,Bai, Jinku,Ai, Tianyu,Zhan, Ye,Li, Guanzhong,Rao, Honghua
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supporting information
p. 4023 - 4028
(2021/05/26)
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- Metal scavenging and catalysis by periodic mesoporous organosilicas with 2,2′-bipyridine metal chelating ligands
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A periodic mesoporous organosilica containing 2,2′-bipyridine (BPy-PMO) was assessed as a metal scavenger and heterogeneous catalyst. The functionalized PMO was synthesized based on a modified version of a previously reported procedure and showed a large
- Waki, Minoru,Inagaki, Shinji
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- Bis(NHC)-Pd-catalyzed one-pot competitive C-C*C-C, C-C*C-O, C-C*C-N, and C-O*C-N cross-coupling reactions on an aryl di-halide catalyzed by a homogenous basic ionic liquid (TAIm[OH]) under base-free, ligand-free, and solvent-free conditions
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Bis(NHC)-Pd-catalyzed competitive asymmetrical C-C*C-C, C-C*C-O, C-C*C-N, and O-C*C-N cross-coupling reactions were performedviathe one-pot strategy in the presence of a new ionic liquid, which played the roles of solvent, base, and ligand simultaneously. The ionic liquid was prepared based on a methyl imidazolium moiety with hydroxyl counter anionsviaa Hofmann elimination on a 1,3,5-triazine framework (TAIm[OH]). Pd ions could be efficiently coordinated through the bis(NHC)-ligand moiety in the ionic liquid. Based on differences in the competitive kinetics of C-C cross-coupling reactions (Heck, Suzuki, and Sonogashira) with C-N and C-O cross-coupling reactions, and also differences in the kinetics of aryl halides, the coupling reactions could be selectively performed with a low amount of by-products. The competitive cross-coupling reactions were thus performed with high selectivity under mild reaction conditions.
- Zhu, Yanfang,Xu, Guiyang,Kazemnejadi, Milad
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p. 11662 - 11671
(2021/07/11)
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- Palladium-catalyzed decarbonylative sonogashira coupling of terminal alkynes with carboxylic acids
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A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.
- Chen, Tieqiao,Huang, Tianzeng,Li, Chunya,Li, Wenhui,Li, Xinyi,Li, Zhaohui,Liu, Long,Tang, Zhi,Zhang, Tao
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supporting information
p. 3304 - 3309
(2021/05/31)
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- One-Pot Dual C?C Coupling Reaction via Site Selective Cascade Formation by PdII-Cryptate of an Amino-Ether Heteroditopic Macrobicycle
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Selectivity of aryl iodo over ethynyl iodo toward the Suzuki cross coupling reaction is explored by utilizing a palladium complex of amino-ether heteroditopic macrobicycle. Subsequently, unreacted ethynyl iodide undergoes homocoupling reaction in the same catalytic atmosphere, thereby representing a cascade dual C?C coupling reaction. Furthermore, this approach is extended for novel one-pot synthesis of unsymmetrical 1,3-diynes.
- Sarkar, Sayan,Sarkar, Piyali,Munshi, Sandip,Ghosh, Pradyut
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p. 7307 - 7314
(2021/03/22)
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- Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions
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A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.
- Niknam, Esmaeil,Panahi, Farhad,Khalafi-Nezhad, Ali
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supporting information
(2021/01/12)
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- A Study of Polarization and Directing Effects of Unsymmetrical Alkynes Using Regioselective Pd-Catalyzed Bromoallylation
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Herein is disclosed the first comprehensive study of factors that affect the regioselectivity of PdBr2(PhCN)2-catalyzed bromoallylation of unsymmetrically substituted internal alkynes. The study was performed on a wide array of electronically and structurally diverse alkynes with aryl-aryl, aryl-ferrocenyl, and aryl-alkyl substitutions. The regioselective formation of bromoallylation products was mostly driven by the polarization of the triple bond in aryl-aryl and aryl-ferrocenyl-substituted ethynes. On the other hand, directing effect, which arises from the presence of a directing group in the side-chain of aryl-alkyl-substituted alkynes, was the dominating factor that determined the regioselectivity of these reactions.
- Topolov?an, Nikola,Hara, Shuto,Císa?ová, Ivana,To?ner, Zdeněk,Kotora, Martin
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supporting information
p. 234 - 240
(2020/01/22)
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- Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes: Synthesis of unsymmetrical diarylethynes
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Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes is described. This reaction not only effectively inhibits the formation of undesired homocoupled products by avoiding the addition of a base, but also exhibits a wide substrate scope to provide a general access to diverse unsymmetrical diarylethynes.
- Chen, Qiang,Fu, Liyan,Nishihara, Yasushi
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supporting information
p. 7977 - 7980
(2020/09/09)
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- Palladium-catalyzed alkynylation of aromatic amines via in situ formed trimethylammonium salts
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A palladium-catalyzed alkynylation of aromatic amines with terminal alkynes via in situ formed trimethylammonium salts is developed. Compared with previous system using ammonium salts as starting materials and high loading of pre-prepared NHC-Pd catalyst (10 mol% Pd), this reaction directly employed amines as the coupling partners and the commercially available Pd2(dba)3/PPh2Cy (1 mol% Pd) as the catalyst, greatly simplifying the manipulation and decreasing the cost.
- Chen, Tieqiao,Huang, Tianzeng,Liu, Long,Yu, Wen-Qing
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supporting information
(2020/02/04)
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- Internal alkyne derivative and preparation method thereof
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The invention belongs to the technical field of organic synthesis, and in particular relates to an internal alkyne derivative and a preparation method thereof. The first aspect of the application provides the internal alkyne derivative, wherein the struct
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Paragraph 0086-0091
(2020/01/25)
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- Ni(acac)2/2,6-bis(diphenylphosphino)pyridine/CuI: A highly efficient palladium-free homogeneous catalyst for the Sonogashira cross-coupling reaction
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A highly efficient palladium-free homogeneous catalyst involving Ni(acac)2/2,6-bis(diphenylphosphino)pyridine ((Ph2P)2py)/CuI components was used for the Sonogashira cross-coupling reaction. The Sonogashira reaction was in
- Ataei, Ali,Daryanavard, Marzieh,Joshaghani, Mohammad,Rafiee, Ezzat
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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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- 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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- Unusual Formation of Cyclopenta[ b]indoles from 3-Indolylmethanols and Alkynes
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Acid-promoted synthesis of cyclopenta[b]indole frameworks from 3-indolylmethanols and alkynes has been reported. The overall transformation represents a formal [3 + 2] annulation via rearrangement. This protocol showed good generality for the carbinol substrates as well as alkynes and allowed the generation of structurally diverse cyclopenta[b]indoles. Terminal alkynes, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituents were found to be not suitable for this transformation. Similarly, N-Ts and N-Boc groups were compatible with reaction conditions, whereas N-Ac and N-Tf failed to undergo this reaction. Isolation of vinyl chloride intermediate suggested the involvement of a vinylic carbocation intermediate. A mechanism has been proposed involving a ring-opening-ring-closing cascade followed by a 1,3-indole migration process via a spirocyclobutene intermediate.
- Gandhi, Soniya,Baire, Beeraiah
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p. 3904 - 3918
(2019/04/25)
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- Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines
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We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.
- Niesobski, Patrik,Martínez, Ivette Santana,Kustosz, Sebastian,Müller, Thomas J. J.
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supporting information
p. 5214 - 5218
(2019/07/31)
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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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- 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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- 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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supporting information
p. 6280 - 6285
(2018/11/23)
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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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p. 3197 - 3204
(2018/08/12)
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- Palladium-Catalyzed Decarbonylative Alkynylation of Amides
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A palladium-catalyzed decarbonylative alkynylation of amides via C-N bond activation is developed. Compared with the reported Ni/Cu catalyzed reaction, which only proceeded well with silylacetylenes, this transformation was also applicable to both aromatic and aliphatic terminal alkynes, including those bearing functional groups, and thus provided a general and straightforward access to diverse internal alkynes.
- Liu, Long,Zhou, Dan,Liu, Min,Zhou, Yongbo,Chen, Tieqiao
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supporting information
p. 2741 - 2744
(2018/05/22)
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- Palladium Nanoparticles Immobilized on Individual Calcium Carbonate Plates Derived from Mussel Shell Waste: An Ecofriendly Catalyst for the Copper-Free Sonogashira Coupling Reaction
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The conversion of waste into high-value materials is considered an important sustainability strategy in modern chemical industries. A large volume of shell waste is generated globally from mussel cultivation. In this work, mussel shell waste (Perna viridis) is transformed into individual calcium carbonate plates (ICCPs) and is applied as a support for a heterogeneous catalyst. Palladium nanoparticles (3–6 nm) are deposited with an even dispersion on the ICCP surface, as demonstrated by X-ray diffraction and scanning electron microscopy. Using this system, Sonogashira cross-coupling reactions between aryl iodides and terminal acetylenes were accomplished in high yields with the use of 1 % Pd/ICCP in the presence of potassium carbonate without the use of any copper metal or external ligand. The Pd/ICCP catalyst could also be reused up to three times and activity over 90 % was maintained with negligible Pd-metal leaching. This work demonstrates that mussel shell waste can be used as an inexpensive and effective support for metal catalysts in coupling reactions, as demonstrated by the successful performance of the Pd-catalyzed, copper-free Sonogashira cross-coupling process.
- Saetan, Trin,Lertvachirapaiboon, Chutiparn,Ekgasit, Sanong,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
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p. 2221 - 2230
(2017/09/06)
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- Sonogashira reaction using arylsulfonium salts as cross-coupling partners
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Triarylsulfonium, alkyl- and fluoroalkyl(diaryl)-sulfonium, and aryl(dialkyl)sulfonium triflates are successfully used as a new family of cross-coupling participants in the Sonogashira reaction as aryldiazonium, diaryliodonium, and tetraphenylphosphonium salts. It was found that terminal alkynes reacted mildly with triarylsulfonium or (2,2,2-trifluoroethyl)diphenylsulfonium triflate at room temperature under Pdand Cu-cocatalysis to give the corresponding arylalkynes in up to >99% yield. This protocol represents the first use of arylsulfonium salts as cross-coupling partners in the Pd/Cu-catalyzed Sonogashira reaction.
- Tian, Ze-Yu,Wang, Shi-Meng,Jia, Su-Jiao,Song, Hai-Xia,Zhang, Cheng-Pan
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p. 5454 - 5457
(2017/11/06)
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- Mesoporous Carbon Supporting Pd (0) as a Highly Efficient and Stable Catalyst for Sonogashira Reaction in Aqueous Media
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Abstract: In this study, palladium (0) nanoparticle supported on mesoporous carbon (Pd/MPC) is prepared by impregnation and H2 reduction. Characterization by XRD, XPS and TEM reveals the mesoporous structure and a high dispersion of palladium nanoparticles (about 4.8?nm) in the mesopores. The catalyst has excellent catalytic activity and stability for Sonogashira reactions of aryl halide (–I, –Br) in aqueous solution. It is noteworthy that Sonogashira reactions of aryl halide (–Cl) can occur by using the novel Pd/MPC catalyst. Meanwhile, the catalyst can be recovered and reused without loss of efficiency until the fifth cycle in water. The fresh catalyst would be of major significance for industrial applications. Graphical Abstract: [Figure not available: see fulltext.]
- Wang, Peng,Wang, Guang-Yu,Qiao, Wen-Long,Feng, Yi-Si
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p. 1792 - 1799
(2016/08/30)
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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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supporting information
p. 1706 - 1710
(2016/04/04)
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- Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes
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A Ni catalytic system was developed for the decarboxylative coupling reaction of alkynyl carboxylic acids with organosilanes. Ni(acac)2 and 1,10-phenanthroline showed the best result in the presence of CsF and CuF2 at 120 °C. This system tolerated the presence of alkyl, alkoxy, halogen, nitro, cyano, ketone, and ester functional groups. Moreover, the reaction with but-2-ynedioic acid and organosilane afforded the corresponding symmetrical diarylalkynes.
- Edwin Raja, Gabriel Charles,Irudayanathan, Francis Mariaraj,Kim, Han-Sung,Kim, Jimin,Lee, Sunwoo
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p. 5244 - 5249
(2016/07/06)
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- Palladium-catalyzed aerobic oxidative cross-coupling of arylhydrazines with terminal alkynes
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The palladium-catalyzed Sonogashira-type aerobic oxidative coupling of arylhydrazines with terminal alkynes via C-N bond cleavage has been developed; internal alkynes were afforded with a broad substrate scope. This reaction proceeds under copper- and base-free conditions with molecular oxygen as the sole oxidant and nitrogen and water as the only by-products.
- Zhao, Yingwei,Song, Qiuling
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supporting information
p. 13272 - 13274
(2015/08/24)
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- Rh-catalyzed decarbonylation of conjugated ynones via carbon-alkyne bond activation: Reaction scope and mechanistic exploration via DFT calculations
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In this full article, detailed development of a catalytic decarbonylation of conjugated monoynones to synthesize disubstituted alkynes is described. The reaction scope and limitation has been thoroughly investigated, and a broad range of functional groups
- Dermenci, Alpay,Whittaker, Rachel E.,Gao, Yang,Cruz, Faben A.,Yu, Zhi-Xiang,Dong, Guangbin
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p. 3201 - 3210
(2015/06/17)
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- PEG Click-Triazole Palladacycle: An Efficient Precatalyst for Palladium-Catalyzed Suzuki-Miyaura and Copper-free Sonogashira Reactions in Neat Water
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A novel water-soluble, phosphine-free PEG click triazole palladacycle has been successfully synthesized. As a precatalyst, the palladacycle exhibited superior catalytic activity towards Suzuki-Miyaura and copper-free Sonogashira cross-coupling in neat water with the turnover numbers (TONs) of up to 9.8×105. In addition, the catalyst could be reused at least 3 times without significant loss of reactivity. A water-soluble PEG click triazole palladacycle has been successfully synthesized. The palladacycle exhibited superior catalytic activity towards Suzuki-Miyaura and copper-free Sonogashira cross-coupling in neat water.
- Zhang, Guofu,Zhang, Wei,Luan, Yuxin,Han, Xingwang,Ding, Chengrong
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supporting information
p. 705 - 710
(2015/12/05)
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- Poly(vinylpyridine)-grafted silica containing palladium or nickel nanoparticles as heterogeneous catalysts for the Sonogashira coupling reaction
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Efficient catalytic systems based on palladium and nickel nanoparticles supported on poly(4-vinylpyridine) (P4VPy)-grafted silica were prepared. After preparation of P4VPy-grafted silica, complexation with PdCl2 and NiCl2 was carried
- Farjadian, Fatemeh,Tamami, Bahman
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p. 1767 - 1773
(2015/02/02)
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- Efficient copper-catalyzed sonogashira couplings of aryl halides with terminal alkynes in water
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An efficient copper-catalyzed method has been developed for Sonogashira couplings of aryl halides with terminal alkynes in water. The protocol uses inexpensive CuBr as the catalyst, 1,10-phenanthroline as the ligand, tetrabutylammonium bromide (TBAB) as the phase-transfer catalyst, environmentally friendly water as the solvent, and various internal alkynes were synthesized in good to excellent yields. Georg Thieme Verlag Stuttgart - New York.
- Yang, Daoshan,Li, Bing,Yang, Haijun,Fu, Hua,Hu, Liming
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scheme or table
p. 702 - 706
(2011/04/26)
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- Copper-catalyzed, aerobic oxidative cross-coupling of alkynes with arylboronic acids: Remarkable selectivity in 2,6-lutidine media
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Aerobic oxidative cross-coupling reactions between alkynes and boronic acids under mild conditions catalyzed by low loadings of a copper salt are reported. 2,6-Lutidine accelerated the reactions dramatically, and the desired coupling products were obtained in high yields with high selectivities.
- Yasukawa, Tomohiro,Miyamura, Hiroyuki,Kobayashi, Sh
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supporting information; experimental part
p. 6208 - 6210
(2011/10/10)
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- Palladium-catalyzed Sonogashira reactions of aryl amines with alkynes via in situ formation of arenediazonium salts
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A general and convenient palladium-catalyzed Sonogashira reaction of in situ generated arenediazonium salts has been developed and various internal arylalkynes are produced in good yields under mild conditions.
- Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
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supporting information; experimental part
p. 7959 - 7961
(2011/08/05)
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- Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids
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A highly efficient and mild palladium-catalyzed decarboxylative cross-coupling of aryl boronic acids and alkynyl carboxylic acids for the synthesis of unsymmetrical substituted alkynes is described for the first time.
- Feng, Chao,Loh, Teck-Peng
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supporting information; experimental part
p. 4779 - 4781
(2010/08/19)
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- Propylene oxide assisted sonogashira coupling reaction
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A propylene oxide assisted base-free Sonogashira cross-coupling reaction has been developed. The unique feature of the current protocol has extended the scope of Sonogashira reaction to some base-sensitive substrates. Georg Thieme Verlag Stuttgart.
- Tong, Zhaolong,Gao, Peng,Deng, Haibing,Zhang, Lei,Xu, Peng-Fei,Zhai, Hongbin
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experimental part
p. 3239 - 3241
(2009/06/19)
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- Gold(I) iodide catalyzed sonogashira reactions
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Gold(I) iodide catalyzed Sonogashira reactions have been developed. Terminal alkynes reacted with aryl iodides and bromides smoothly in the presence of AuI (1 mol-%) and dppf (1 mol-%) in toluene to generate the corresponding cross-coupling products in good to excellent yields. Furthermore, aromatic terminal alkynes could also react with 2-iodoaniline to form substituted indoles in excellent yields through a coupling-cyclization reaction sequence under the present reaction conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Li, Pinhua,Wang, Lei,Wang, Min,You, Feng
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scheme or table
p. 5946 - 5951
(2009/05/27)
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- Palladium-catalyzed copper-free sonogashira coupling reaction in water and acetone
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An efficient palladium-catalyzed copper-free Sonogashira reaction in water and acetone has been developed under mild conditions. The results showed that the aryl iodides could carry out the cross-coupling reaction with a variety of terminal alkynes in high yields in water-acetone in the absence of amine, copper(I) salts, or phosphine ligands at 60°C for one hour, and good yields were obtained for aryl bromides at 60°C for 12-24 hours in the presence of triphenylphosphine and piperidine. The method could be used to synthesize polyethynyl aromatic compounds in a one-pot reaction. Georg Thieme Verlag Stuttgart.
- Shi, Shengyin,Zhang, Yuhong
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p. 1843 - 1850
(2008/02/10)
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- An amine-, copper- and phosphine-free Sonogashira coupling reaction catalyzed by immobilization of palladium in organic-inorganic hybrid materials
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An immobilization of palladium in organic-inorganic hybrid materials-catalyzed Sonogashira coupling reaction has been described. Terminal alkynes reacted with aryl iodides and aryl bromides only in the presence of a 3-(2-aminoethylamino)-propyl-functionalized, silica gel-immobilized palladium catalyst under amine-, copper- and phosphine-free reaction conditions. The reaction generates the corresponding cross-coupling products in excellent yields. Furthermore, the silica-supported palladium can be recovered and recycled by a simple filtration of the reaction solution and used for 30 consecutive trials without any decreases in activity.
- Li, Pin-Hua,Wang, Lei
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p. 681 - 685
(2007/10/03)
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- A novel silver iodide catalyzed sonogashira coupling reaction
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A novel and efficient Ag-catalyzed Sonogashira coupling reaction has been developed. Terminal alkynes couple with aryl iodides and aryl bromides in the presence of silver iodide, tri-phenylphosphine and potassium carbonate to afford the corresponding cross-coupling products in high yields. Georg Thieme Verlag Stuttgart.
- Li, Pinhua,Wang, Lei
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p. 2261 - 2265
(2007/10/03)
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- Application of recoverable nanosized palladium(0) catalyst in Sonogashira reaction
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In the absence of ligand, copper and amine, a recoverable nanoparticle palladium(0) catalyzed Sonogashira reaction of aryl iodides and bromides with terminal alkynes was developed. The protocol involved the use of an environmental-friendly reaction system with ethanol as the solvent, potassium carbonate as a base, and poly(vinylpyrrolidone) (PVP) supported nanosized palladium metal colloids as the catalyst. The palladium metal was recovered and recycled by a simple decantation of the reaction solution and used for eight consecutive trials without significant loss of its reactivity.
- Li, Pinhua,Wang, Lei,Li, Hongji
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p. 8633 - 8640
(2007/10/03)
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- New synthetic applications of indium organometallics in cross-coupling reactions
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The use of indium organometallics in multifold and sequential cross-coupling reactions is reported. Triorganoindium reagents (R3In) react, under palladium catalysis, with oligohaloarenes affording the multiple cross-coupling products in a single operation. In the reaction, the three organic groups (alkyl, aryl, alkenyl or alkynyl) attached to indium are efficiently transferred to the electrophile, with only a slight excess of organometallic reagent. We demonstrate that indium organometallics are useful reagents for sequential cross-coupling reactions. This reaction illustrates the high chemoselectivity of R3In. Georg Thieme Verlag Stuttgart.
- Pena, Miguel A.,Perez Sestelo, Jose,Sarandeses, Luis A.
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p. 485 - 492
(2007/10/03)
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- Process for preparing alkynyl-substituted aromatic and heterocyclic compounds
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Mono- and disubstituted aryl or heterocyclic acetylenes are produced by a process comprising reacting an aryl nitrile with an alkynylzinc compound, a bis-alkynylzinc compound, or an alkynylmagnesium compound, in the presence of a nickel/phosphine catalyst.
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Page/Page column 9
(2010/02/12)
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- Tetraorganoindates as Nucleophilic Coupling Partners in Pd-Catalyzed Cross-Coupling Reactions
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(Equation presented) In situ generated ate complex In situ-generated tetraorganoindate complexes from the reaction of 1 equiv of indium trichloride with 4 equiv of appropriate organometallics are efficient nucleophiles in Pd-catalyzed cross-coupling reactions. In this novel reaction tetraorganoindates containing methyl, 1°- and 2°-alkyl, vinyl, alkynyl, and aryl groups transfer the four organic groups to a variety of electrophiles with high atom efficiency.
- Lee, Phil Ho,Lee, Sung Wook,Seomoon, Dong
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p. 4963 - 4966
(2007/10/03)
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- Multifold and sequential cross-coupling reactions with indium organometallics
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Multifold and sequential palladium-catalyzed cross-coupling reactions can be performed between triorganoindium compounds and oligohaloarenes using only a small excess of the organometallic reagent, low catalyst charge loading and short reaction times.
- Pena, Miguel A.,Perez, Ignacio,Perez Sestelo, Jose,Sarandeses, Luis A.
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p. 2246 - 2247
(2007/10/03)
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- Nucleophilic Desulfinylation of α-Fluoro-β-(alkoxy and silyloxy) Sulfoxides. Effects of the β-Oxy Substituent on Protonation, 1,2-Hydrogen Migration, and Nucleophile Addition to the Fluorocarbenoid Centers
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Treatment of 2-(4-biphenylyl)-2-t-butyldimethylsilyloxy-1-chloro-1-fluoroethyl phenyl sulfoxide with PhMgBr resulted in the formation of a fluorostilbene derivative, a fluoro enol silyl ether and small amounts of 4-(fluoroacetyl)biphenyl, while a similar
- Uno, Hidemitsu,Sakamoto, Katsuji,Suzuki, Hitomi
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p. 218 - 227
(2007/10/02)
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- Synthesis of Some New Polynuclear Compounds by Cycloaddition Reaction
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A large number of 7,9-disubstituted derivatives (I) of cyclopentacenaphthylene-8(H)-one and 2,5-disubstituted derivatives (II) of 3,4-diphenylcyclopentadienone have been synthesized by condensing acenaphthaquinone and benzil separately with suitable 1,3-disubstituted propan-2-ones.The 3-(o- and p-methoxytolyl)cyclopentadienones (IX) have been synthesized by Friedel-Crafts reaction of appropriate methyl cresyl ethers and phenacyl chloride.These dienones have been subjected to Diels-Alder reaction with acenaphthylene and a new acetylenic dienophile (V) (whose synthesis is also described in this paper) to yield a large number of polynuclear aromatic compounds having fluoranthene and p-quaterphenyl nuclei, which have been finally characterised by elemental analyses, IR and PMR spectral data.
- Samanta, S. R.,Mukherjee, A. K.
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