22666-07-5Relevant articles and documents
A mild copper-mediated Glaser-type coupling reaction under the novel CuI/NBS/DIPEA promoting system
Li, Lingjun,Wang, Jiuxia,Zhang, Guisheng,Liu, Qingfeng
, p. 4033 - 4036 (2009)
A simple copper promoting system CuI/NBS/DIPEA was first found to efficiently promote Glaser coupling reaction under ambient temperature. The alkynes with sensitive groups such as acetal and ketal, TBDMS, ester and amide could react smoothly to afford the
Application of iodanes to the dimerization of terminal alkynes
Yan, Jie,Lin, Feng,Yang, Zhenping
, p. 1301 - 1303 (2007)
The dimerization of terminal acetylenes was studied using iodanes as oxidants under palladium-catalyzed conditions. It was found that a number of iodanes were useful in the reaction, with (diacetoxyiodo)benzene and iodosylbenzene being the best oxidants.
Formation of Dimeric Acetylenes: an Unexpected Reaction of Acetylenic Selenides
Comasseto, Joao V.,Catani, Valdomiro,Ferreira, Jose T. B.,Braga, Antonio L.
, p. 1067 (1986)
1-Selenoalk-1-ynes react with m-chloroperbenzoic acid in tetrahydrofuran- water furnishing 1,4-disubstituted 1,3-diynes free of selenium in high yield.
Cu(II)-CMC: A mild, efficient and recyclable catalyst for the oxidative alkyne homocoupling reaction
Jiang, Yuqin,Guo, Niu,Li, Xiyong,Sun, Yamin,Zhang, Weiwei
, p. 549 - 554 (2017)
Cu(II) heterogenized on sodium carboxymethyl cellulose (Na-CMC) has been thoroughly characterized by different techniques. Cu(II)-CMC has been applied for the first time in the homocoupling reaction of a variety of terminal alkynes. The catalyst furnished
First example of transition-metal-free Glaser-type coupling reaction
Yan, Jincan,Wang, Lei
, p. 2333 - 2338 (2005)
In the presence of potassium tert-butoxide and in toluene, 1,1-dibromo-1-alkenes smoothly generated the corresponding Glaser-type coupling-reaction products (1,3-diynes) in moderate to good yields. Copyright Taylor & Francis, Inc.
Ligand-free copper-catalyzed synthesis of symmetrical diynes from 1,1-dibromo-1-alkenes
Jin, Hui,Kuang, Chunxiang
, p. 592 - 594 (2011)
Symmetrical diynes were synthesized by ligand-free copper-catalyzed homocoupling reaction of 1,1-dibromo-1-alkenes using a DBU/DMSO system at room temperature in good to excellent yields.
Nickel-Copper-Catalyzed C(sp2)- N Cross-Coupling of Cyclic and Bridged Amides: An Access to Cyclic Enamides and Alkenyl Vince Lactams
Maity, Pintu,Kundu, Debasish,Ranu, Brindaban C.
, p. 3617 - 3626 (2015)
An efficient C(sp2)- N cross-coupling of styrenyl and vinyl halides with cyclic and bridged amides catalyzed by nickel acetonylacetonate [Ni(acac)2] and copper(I) iodide (CuI) in the absence of any ligand has been developed. The reaction conditions are optimized to give the maximum yield of products using cesium carbonate (Cs2CO3) (2.0 equiv.) in N-methyl-2-pyrrolidinone (NMP) at 110 C under argon in the presence of Ni(acac)2/CuI (10 mol% each). A series of alkenyl derivatives of Vince lactams (bridged amides) and cyclic amides are obtained by this procedure. Halogen-containing styrenyl bromides also underwent coupling with amides to provide the products. The coupling is highly chemoselective as during the reactions the halogens (Br, Cl, F) on the aromatic ring remained intact and these can be used for further functionalization to make these enamides more useful. Although the (E)-styrenyl halides produced the corresponding (E)-styrenyl enamides, reactions with (Z)-styrenyl halides produced 1,3-di-ynes instead of (Z)-styrenyl enamides. This may be explained by the possibility of E2 type elimination of (Z)-styrenyl halides in the presence of a strong base like cesium carbonate followed by homocoupling. This catalyst system works efficiently for the N-arylation too along with N-styrenylation and vinylation. The bridged as well as cyclic amides successfully coupled with substituted aryl halides to provide the corresponding products. In general, the reactions are clean and high yielding. The operations are very simple and the products are obtained pure by standard column chromatography. The reaction is compatible with variety of amides and alkenyl bromides. The roles of nickel acetonylacetonate and copper(I) iodide in this reaction have been established and a possible reaction pathway has been outlined. The significant feature of this protocol is the alkenylation of Vince lactams via C(sp2)- N cross-coupling, which has not been reported so far and these products may have much potential in the pharmaceutical industry.
Mesoporous silica-supported copper-catalysts for homocoupling reaction of terminal alkynes at room-temperature
Li, Hongling,Yang, Min,Zhang, Xia,Yan, Liang,Li, Jing,Qi, Yanxing
, p. 1343 - 1349 (2013)
Amine-functionalized mesoporous silica-supported copper catalysts SBA-15@amine-Cu and SBA-15@Oamine-Cu were prepared and proved to be efficient and reusable for homocoupling of terminal alkynes at room temperature with air as the oxidant. SBA-15@amine-Cu exhibited better recyclability than SBA-15@Oamine-Cu. The differences in the catalytic performances of the catalysts could be ascribed to catalyst structure and the interaction between copper and the supports. The as-prepared catalysts were systematically characterized by inductively coupled plasma atomic emission spectroscopy (ICP-AES), high resolution-transmission electron microscopy (HRTEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS) and nitrogen physical adsorption. The analysis indicated that the mesoporous structure of the materials was retained during the immobilization process. XPS results suggested that the as-prepared catalysts were not obtained by a simple physical adsorption of CuCl on the supports. It is noted that, for aliphatic alkynes, the catalytic activity of SBA-15@amine-Cu is even higher than that of the homogeneous copper catalytic system and that of some previously reported heterogeneous systems.
Palladium-catalysed coupling of 4-halopyrrolo[2,3-d]pyrimidines with arylacetylenes: Synthesis of a new heterocyclic system - 4H-pyrrolo[2,3,4-de] pyrimido[5′,4′:5,6][1,3]diazepino[1,7-a]indole
Tumkevicius, Sigitas,Masevicius, Viktoras
, p. 2327 - 2330 (2004)
Palladium-catalysed reaction of methyl 5-amino-4-chloro(or iodo)-7-methyl-2-methylthiopyrrolo[2,3-d]pyrimidine-6-carboxylate with arylacetylenes affords the corresponding 4-(arylethynyl)pyrrolopyrimidines. Reaction of 5-amino-4-iodopyrrolopyrimidine with
Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling
Mishra, Nidhi,Singh, Sumit K.,Singh, Anoop S.,Agrahari, Anand K.,Tiwari, Vinod K.
, p. 17884 - 17895 (2021/12/17)
Glycosyl triazoles have been introduced as efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect t
Leaf-like CuO nanosheets on rGO as an efficient heterogeneous catalyst for Csp-Csp homocoupling of terminal alkynes
Gao, Lingfeng,Wang, Bin,Zheng, Gengxiu
, (2020/12/21)
In this work, the economic and well-defined leaf-like CuO nanosheets on rGO (CuO nanosheets/rGO) was synthesized by a convenient hydrothermal method. The morphology and chemical composition of CuO nanosheets/rGO were confirmed by XRD, SEM-EDS, TEM, HR-TEM, and XPS techniques. The CuO nanosheets/rGO was successfully applied as a high-performance heterogeneous catalyst in the homocoupling of 12 terminal alkynes, and the isolated yield of each product was more than 80%, except for propargyl alcohol. This catalyst could be reused five times with little activity loss. Thus, it is beneficial for green and sustainable development of organic synthetic chemistry.
Synergistic Effect of NiLDH@YZ Hybrid and Mechanochemical Agitation on Glaser Homocoupling Reaction
Mokhtar, Mohamed,Alzhrani, Ghalia,Aazam, Elham S.,Saleh, Tamer S.,Al-Faifi, Sulaiman,Panja, Subir,Maiti, Debabrata
supporting information, p. 8875 - 8885 (2021/05/19)
Herein, we report the synthesis of nickel-layered double hydroxide amalgamated Y-zeolite (NiLDH@YZ) hybrids and the evaluation of the synergistic effect of various NiLDH@YZ catalysts and mechanochemical agitation on Glaser homocoupling reactions. Nitrogen
