1129-65-3Relevant articles and documents
Tokuda et al.
, p. 606 (1976)
Copper-catalyzed coupling reaction of terminal alkynes with aryl- and alkenyliodonium salts
Kang, Suk-Ku,Yoon, Seok-Keun,Kim, Young-Mook
, p. 2697 - 2699 (2001)
(Equation presented) The copper iodide-catalyzed cross-coupling of terminal alkynes with hypervalent iodonium salts was accomplished with Cul (10 mol %) and NaHCO3 (2 equiv) in DME/H2O (4:1) at room temperature for 30 min to afford arylalkynes or enynes under mild conditions.
A convenient high activity catalyst for the Sonogashira coupling of aryl bromides
Koellhofer, Axel,Plenio, Herbert
, p. 1295 - 1300 (2005)
A mixture of Na2PdCl4, CuI and (t-Bu) 3PH+BF4- (molar ratio 4:3:8) dispersed in H2N(i-Pr)2 Br can be used as a "single source" precatalyst for the Sonogashira coupling of aryl bromides with various aryl- and alkylacetylenes in HN(i-Pr)2 solvent. Arylacetylenes require just 0.005 mol % of Pd catalyst at 80°C, with TOFs ranging between 3,200 and 10,000 h-1.
A copper-free Sonogashira reaction using nickel ferrite as catalyst in water
Moghaddam, Firouz Matloubi,Tavakoli, Ghazal,Rezvani, Hamid Reza
, p. 82 - 87 (2015)
The Sonogashira reaction using nickel ferrite nanoparticles as catalyst and under copper-free conditions was investigated in water as a green solvent. Various types of aryl and alkyl halides were successfully coupled with phenyl acetylene under the optimized reaction conditions with very good to excellent yields at a short time. The catalyst is easily recoverable and can be reused for several runs with a good turnover number.
Rhodium-catalyzed synthesis of indenols by regioselective coupling of alkynes with ortho-carbonylated arylboronic acids
Shintani, Ryo,Okamoto, Kazuhiro,Hayashi, Tamio
, p. 1294 - 1295 (2005)
A rhodium/diene-catalyzed regioselective synthesis of indenols has been developed through the coupling of alkynes with ortho-carbonylated arylboronic acids. These reactions proceed under mild conditions in uniformly high yield and regioselectivity. The re
Organic functionalization of mesopore walls in hierarchically porous zeolites
Lee, Dong-Hwan,Choi, Minkee,Yu, Byung-Woo,Ryoo, Ryong
, p. 74 - 76 (2009)
Mesopore walls of hierarchically meso-/microporous zeolites (MFI, BEA and LTA) are covered with silanol groups, so that the zeolites can be functionalized with various organic groups via silylation; the organic-functionalized hierarchical zeolites exhibit
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Naruse,M. et al.
, p. 1847 - 1850 (1973)
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Gallic acid-derived palladium(0) nanoparticles as in situ-formed catalyst for Sonogashira cross-coupling reaction in ethanol under open air
Sarmah, Manashi,Mondal, Manoj,Gohain, Shivanee Borpatra,Bora, Utpal
, p. 31 - 34 (2017)
A simple and eco-friendly protocol using gallic acid-derived palladium(0) nanoparticles as in situ-formed catalyst for Sonogashira reactions in ethanol under optimum thermal conditions have been developed. Excellent yields were obtained with the addition of a small amount of gallic acid (1 mol%) to the reaction mixture. The formation of the PdNPs was confirmed by using UV/Vis spectroscopy, and their size and morphology were determined by TEM and XRD analysis. Both aliphatic and aromatic terminal alkynes displayed efficient reactivity with the catalytic system. Moreover, the reaction condition is highly compatible with less reactive aryl bromides at moderate temperature, and further can be reused repeatedly up to four cycles. Since gallic acid is a non-toxic naturally abundant phytochemical, the present method provides an efficient alternative route for Sonogashira reaction with natural feedstock as additive.
FRE RADICAL SUBTITUTION REACTIONS OF PHENYLACETYLENE DERIVATIVES BY AN ADDITION-ELIMINATION MECHANISM
Russell, Glen A.,Ngoviwatchai, Preecha
, p. 3479 - 3482 (1986)
Phenylacetylenes (PhCCQ with Q=PhSO2, I, SPh, Bu3Sn PhCCHg) undergo free radical chain substitution reactions with RHgCl, R2Hg, (EtO)2P(O)HgCl, (PhS)2Hg or (PhSO2)2Hg.The relative reactivities of PhCCQ towards c-C6H11 . are Q = PhSO2 (
A new mild procedure for the direct coupling of 1-trimethylsilyl acetylenes with vinyl triflates or aryl iodide
Halbes, Ulla,Pale, Patrick
, p. 2039 - 2042 (2002)
1-Trimethylsilyl acetylenes can be directly coupled with vinyl triflates or aryl iodide in the presence of the appropriate amount of potassium carbonate and methanol and a catalytic amount of AgCl and Pd(PPh3)4. Functionalized enynes can thus be obtained in good to excellent yields without prior deprotection of the alkyne.
Copper-catalyzed coupling of aryl halides with terminal alkynes in the presence of KF/Al2O3
Hosseinzadeh, Rahman,Mohadjerani, Maryam,Tavakoli, Rahmatollah,Alikarami, Mohammad
, p. 282 - 288 (2010)
A convenient catalyst system consisting of copper iodide, L-proline, and potassium fluoride/Al2O3 was effective for the coupling reaction of aryl iodides and bromides with terminal alkynes. In contrast to the conventional Sonogashira
FeCl3/PPh3-catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes
Sawant, Dinesh N.,Tambade, Pawan J.,Wagh, Yogesh S.,Bhanage, Bhalchandra M.
, p. 2758 - 2761 (2010)
Conditions for a FeCl3/PPh3-catalyzed and palladium-, copper-, amine free-Sonogashira coupling reaction of aryl halides with terminal alkynes are reported. The protocol was applicable to a wide variety of substituted aryl iodides and alkynes with different steric and electronic properties and gave excellent yields of the desired coupling products.
Mortreux et al.
, p. 4967 (1978)
A copper- and amine-free Sonogashira reaction employing aminophosphines as ligands
Cheng, Jiang,Sun, Yanhui,Wang, Feng,Guo, Minjie,Xu, Jian-Hua,Pan, Yi,Zhang, Zhaoguo
, p. 5428 - 5432 (2004)
An efficient Pd-catalyzed Sonogashira coupling reaction was achieved in the absence of a copper salt or amine with an inorganic base and easily prepared, air-stable aminophosphine ligands in commonly used organic solvents; good to excellent yields were ob
Rh(iii)-Catalyzed olefination to build diverse oxazole derivatives from functional alkynes
He, Yuan,Zheng, Ting,Huang, Yin-Hui,Dong, Lin
, p. 4937 - 4942 (2021)
A novel Rh(iii)-catalyzed olefination reaction of oxazoles to generate diverse oxazole skeleton derivatives has been realized by directly using oxazole as the directing group. The reaction could tolerate many functional groups, affording complex oxazole derivatives with long chain alkenyls in moderate to good yields, which might find applications in the construction of diverse compounds.
Fast heck-cassar-sonogashira (hcs) reactions in green solvents
Cabri, W.,Corbisiero, D.,Daka, A.,Fantoni, T.,Ferrazzano, L.,Martelli, G.,Ricci, A.,Tolomelli, A.,Viola, A.
, p. 3969 - 3973 (2020)
The replacement of toxic solvents with greener alternatives in Heck-Cassar-Sonogashira (HCS) cross-couplings was investigated. The fine-tuning of the HCS protocol allowed to achieve complete conversions and high speed under mild conditions. N-Hydroxyethylpyrrolidone (HEP) gave the best results. Moreover, the methodology was successfully applied to the synthesis of an intermediate of the anticancer drug Erlotinib, demonstrating the versatility of the new green protocol.
A novel Pd/Ag-catalyzed sonogashira coupling reaction of terminal alkynes with hypervalent iodonium salts
Zhu, Min,Zhou, Zhongshi,Chen, Rui
, p. 2680 - 2682 (2008)
A novel and fast Sonogashira coupling reaction of terminal alkynes with hypervalent iodonium salts was achieved in the presence of catalytic amount of palladium chloride and silver(I) iodide, providing a convenient method for the synthesis of aryl-alkynes in good yields in a short time. Georg Thieme Verlag Stuttgart.
Facile synthesis of palladium nanoclusters and their catalytic activity in Sonogashira coupling reactions
Athilakshmi,Ramanathan,Chand, Dillip Kumar
, p. 5286 - 5288 (2008)
This work reports a facile synthesis of palladium nanoclusters (PdNCs) in MeCN/MeOH mixture without any stabilizer. The PdNCs were found to be effective catalysts for copper-free, amine-free and ligand-free Songashira coupling reactions under ambient cond
Nickel-catalyzed alkynylation of aryl iodides (Sonogashira Reaction) in water
Bakherad, Mohammad,Keivanloo, Ali,Mihanparast, Samira
, p. 179 - 185 (2010)
The Sonogashira coupling of terminal acetylenes with aryl iodides, catalyzed by Ni-Cu, in the presence of sodium lauryl sulfate as the surfactant and cesium carbonate as the base, in water, leads to the formation of aryl alkyne products.
A new, efficient, and inexpensive copper(II)/salicylic acid complex catalyzed Sonogashira-type cross-coupling of haloarenes and iodoheteroarenes with terminal alkynes
Chen, Horung-Jyh,Lin, Zhe-Yi,Li, Meng-Yuan,Lian, Ruei-Jheng,Xue, Qing-Wen,Chung, Jui-Lun,Chen, Shu-Chih,Chen, Yao-Jung
, p. 7755 - 7761 (2010)
A new, efficient, and inexpensive CuCl2/salicylic acid catalytic system has been developed to catalyze Sonogashira-type cross-coupling of haloarenes and iodoheteroarenes with terminal alkynes under mild reaction conditions to afford the corresponding coupling products in 18-95% yields. The role of salicylic acid might act as a bidentate O,O-donor ligand to activate the catalytic reactivity of copper chloride in coupling reactions was also briefly discussed.
Solvent effects in the Grignard reaction with alkynes
Tuulmets,Paellin,Tammiku-Taul,Burk,Raie
, p. 701 - 705 (2002)
Kinetic studies were carded out on the reaction of phenylmagnesium bromide with hex-1-yne in diethyl ether, and in binary mixtures of diethyl ether with toluene, chlorobenzene and dichloromethane. The reaction was accelerated by addition of non-donating solvents. The replacement of a coordinated solvent molecule by the alkyne is necessary for the reaction to proceed, according to density functional theory (DFT) calculations with B3LYP/6-31 + G* method. The non-donating solvents accelerate the reaction by shifting the replacement equilibrium in favour of the complex formation. An analysis in terms of the Koppel-Palm equation revealed a rate decrease with increase in solvent polarity and polarizability. Copyright
A Pd NP-confined novel covalent organic polymer for catalytic applications
Yadav, Deepika,Awasthi, Satish Kumar
, p. 1320 - 1325 (2020)
A novel unsymmetrical covalent organic polymer, COP (1), was designed and characterized using several analytical and spectroscopic techniques. COP (1) was synthesized via the nucleophilic substitution reaction of 2,4,6-trichloro-1,3,5-triazine with p-amin
Palladium-catalysed coupling of terminal alkynes with aryl halides aided by catalytic zinc
Crisp, Geoffrey T.,Turner, Peter D.,Stephens, Kim A.
, p. 219 - 224 (1998)
The palladium-catalysed coupling of aryl halides with terminal alkynes can be performed using base, zinc chloride and sodium iodide. This protocol represents a convenient method for the generation of nucleophilic acetylides in situ.
Borane catalysed cyclopropenation of arylacetylenes
Dasgupta, Ayan,Heard, Matthew J.,Melen, Rebecca L.,Stefkova, Katarina
supporting information, p. 6736 - 6739 (2021/07/13)
Triarylboranes have gained substantial attention as catalysts for C-C bond forming reactions due to their remarkable catalytic activities. Herein, we report B(C6F5)3catalysed cyclopropenation of a wide variety of arylacetylenes using donor-acceptor diazoesters. A mild reaction protocol has been developed for the synthesis of functionalised cyclopropenes (33 examples) in good to excellent yields.
An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne cis-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis
Huang, Zhidao,Wang, Yulei,Leng, Xuebing,Huang, Zheng
supporting information, p. 4824 - 4836 (2021/04/07)
The selective synthesis of Z-alkenes in alkyne semihydrogenation relies on the reactivity difference of the catalysts toward the starting materials and the products. Here we report Z-selective semihydrogenation of alkynes with ethanol via a coordination-induced ionic monohydride mechanism. The EtOH-coordination-driven Cl- dissociation in a pincer Ir(III) hydridochloride complex (NCP)IrHCl (1) forms a cationic monohydride, [(NCP)IrH(EtOH)]+Cl-, that reacts selectively with alkynes over the corresponding Z-alkenes, thereby overcoming competing thermodynamically dominant alkene Z-E isomerization and overreduction. The challenge for establishing a catalytic cycle, however, lies in the alcoholysis step; the reaction of the alkyne insertion product (NCP)IrCl(vinyl) with EtOH does occur, but very slowly. Surprisingly, the alcoholysis does not proceed via direct protonolysis of the Ir-C(vinyl) bond. Instead, mechanistic data are consistent with an anion-involved alcoholysis pathway involving ionization of (NCP)IrCl(vinyl) via EtOH-for-Cl substitution and reversible protonation of Cl- ion with an Ir(III)-bound EtOH, followed by β-H elimination of the ethoxy ligand and C(vinyl)-H reductive elimination. The use of an amine is key to the monohydride mechanism by promoting the alcoholysis. The 1-amine-EtOH catalytic system exhibits an unprecedented level of substrate scope, generality, and compatibility, as demonstrated by Z-selective reduction of all alkyne classes, including challenging enynes and complex polyfunctionalized molecules. Comparison with a cationic monohydride complex bearing a noncoordinating BArF- ion elucidates the beneficial role of the Cl- ion in controlling the stereoselectivity, and comparison between 1-amine-EtOH and 1-NaOtBu-EtOH underscores the fact that this base variable, albeit in catalytic amounts, leads to different mechanisms and consequently different stereoselectivity.
