126309-76-0Relevant academic research and scientific papers
Hydrazone-promoted Sonogashira coupling reaction with aryl bromides at low palladium loadings
Mino, Takashi,Suzuki, Saori,Hirai, Kiminori,Sakamoto, Masami,Fujita, Tsutomu
, p. 1277 - 1280 (2011)
The Sonogashira coupling reaction of aryl bromides with a variety of terminal alkynes in DMSO at 125 C gave internal arylated alkynes using low-loaded Pd(acac)with hydrazone as a ligand and CuI as the co-catalyst in good yields. Georg Thieme Verlag Stuttgart · New York.
Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids
Abrams, J. N.,Chi, B. K.
, p. 1236 - 1244 (2020)
Abstract: The reaction of simple alkynoate salts with isolated arenediazonium tetrafluoroborate salts that had been pre-conditioned with the gold(I) catalyst AuCl(Me2S) led to the formation of cross-coupled products via a decarboxylative Sonogashira reaction process in modest yield and under mild conditions. The major by-product is a defunctionalized aryl moiety stemming from the diazonium salt, which competitively forms via hydrodediazonation. Good functional group tolerance and reaction site selectivity were attained in this limited investigation.
Insights into Sonogashira cross-coupling by high-throughput kinetics and descriptor modeling
An Der Heiden, Markus R.,Plenio, Herbert,Immel, Stefan,Burello, Enrico,Rothenberg, Gadi,Hoefsloot, Huub C. J.
, p. 2857 - 2866 (2008)
A method is presented for the high-throughput monitoring of reaction kinetics in homogeneous catalysis, running up to 25 coupling reactions in a single reaction vessel. This method is demonstrated and validated on the Sonogashira reaction, analyzing the k
Alkynylation of aryl halides with perfluoro-tagged palladium nanoparticles immobilized on silica gel under aerobic, copper- and phosphine-free conditions in water
Bernini, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Forte, Giovanni,Petrucci, Francesco,Prastaro, Alessandro,Niembro, Sandra,Shafir, Alexandr,Vallribera, Adelina
, p. 2270 - 2273 (2009)
The utilization of perfluoro-tagged palladium nanoparticles immobilized on fluorous silica gel through fluorous-fluorous interactions (Pd np-A/FSG) or linked to silica gel by covalent bonds (Pd np-B) in the alkynylation of terminal a
[Cu(acac)2]·H2O-catalyzed sonogashira-type couplings of aryl halides and terminal alkynes
Li, Tingyi,Qu, Xiaoming,Xie, Guanlei,Mao, Jincheng
, p. 1325 - 1330 (2011)
Highly selective coupling of aryl halides with terminal alkynes can be conducted using low-cost and readily available [Cu(acac)2] ·H2O under palladium- and amine-free conditions. This protocol makes the typical Sonogashira reaction more practical and useful (TBAB=tetrabutyl ammonium bromide; DMSO=dimethyl sulfoxide; see scheme). Copyright
Continuous biphasic catalysis: Palladium catalyzed cross coupling reactions
Hillerich, Jens,Plenio, Herbert
, p. 3024 - 3025 (2003)
The immobilisation of polymer tagged catalysts in a stationary solvent in a reactor and the flow of reactants dissolved in another immiscible solvent through it, allows the conversion of a continuous feed of reactants into a product stream, as exemplified
An Efficient and Recyclable Mesostructured Polymer-Supported N-Heterocyclic Carbene-Palladium Catalyst for Sonogashira Reactions
Yu, Tao,Li, Ying,Yao, Chengfu,Wu, Haihong,Liu, Yueming,Wu, Peng
, p. 1712 - 1718 (2011)
Palladium catalyst systems are the most widely used for the formation of C-C and C-N bonds. Environmentally friendly heterogeneous palladium catalysts have strongly stimulated growth in this research area. Herein, a FDU (Fudan University)-15 mesopolymer w
An amine-, copper- and phosphine-free Sonogashira coupling reaction catalyzed by immobilization of palladium in organic-inorganic hybrid materials
Li, Pin-Hua,Wang, Lei
, p. 681 - 685 (2006)
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.
The use of a bifunctional copper catalyst in the cross-coupling reactions of aryl and heteroaryl halides with terminal alkynes
Wu, Minyan,Mao, Jincheng,Guo, Jun,Ji, Shunjun
, p. 4050 - 4054 (2008)
Copper-catalyzed cross-coupling reactions of aryl halides and heteroaryl halides with terminal alkynes were carried out in DMF at 110-130 °C to provide the corresponding coupling products in satisfactory-to-good yields by using inexpensive 8-hydoxyquinoline as the ligand. Noteworthy is that the bifunctional copper catalyst was successfully applied in this alkynylation reaction for the first time. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Rapid and highly selective copper-free sonogashira coupling in high-pressure, high-temperature water in a microfluidic system
Kawanami, Hajime,Matsushima, Keiichiro,Sato, Masahiro,Ikushima, Yutaka
, p. 5129 - 5132 (2007)
All in a whirl: A reaction system based on "step-by-step rapid mixing and heating" with high-pressure, high-temperature water has been applied to an extremely efficient Sonogashira coupling (see picture). No organic solvents or ligands for the Pd catalyst
