62856-06-8Relevant academic research and scientific papers
A facile protocol for copper-free palladium-catalyzed Sonogashira coupling in aqueous media
Jung, Da-Young,Park, Soo Youl,Kim, Seung-Hoi
supporting information, p. 110 - 116 (2021/11/09)
The combination of a readily available palladium catalyst and an eco-friendly basic aqueous solution of room-temperature ionic liquid, choline hydroxide (ChOH), was used in a facile protocol alternative to the Sonogashira coupling reaction, alkynylation of aryl halides in the absence of a copper cocatalyst and an external base. The dual nature of ChOH to act as a base and a green solvent played a crucial role in the catalytic cycle. The coupling reaction progressed efficiently to form a Csp-Csp2 bond under the identified conditions although the reaction outcome depended significantly on the substrates.
Magnetic chitosan-functionalized cobalt-NHC: Synthesis, characterization and catalytic activity toward Suzuki and Sonogashira cross-coupling reactions of aryl chlorides
Hajipour, Abdol R.,Malek, Shaghayegh Sadeghi
, (2021/04/23)
Aryl chlorides are one of the most stable and available electrophiles, however, their coupling with nucleophiles remains a challenge in organic synthesis. Herein, we prepared a Cobalt-NHC (N-Heterocyclic carbene) complex anchored on magnetic chitosan nanoparticles and assayed its catalytic activity for the reactions of substituted phenylboronic acid and also phenlacetylene with derivatives of aryl chlorides. These reactions are of great importance since they are employed for the synthesis of unsymmetrical diarylethynes and biphenyls, which belong to a prime class of building blocks. The synthesized nanocatalyst was found to be highly efficient in Suzuki and Sonogashira coupling in terms of their activity and recyclability in polyethylene glycol (PEG) as a green reaction media under conditions of temperatures (70 and 100 °C) and Co loading (3 and 6 mol%). To the best of our knowledge, this is the first attempt of using cobalt-NHC complex for catalyzing the abovementioned reactions. Moreover, replacing the earth-abundant Cobalt-based catalyst as an alternative to high cost palladium make this approach promising from sustainable chemistry view.
Nickel-Catalyzed Sonogashira C(sp)-C(sp2) Coupling through Visible-Light Sensitization
Zhu, Da-Liang,Xu, Ruijie,Wu, Qi,Li, Hai-Yan,Lang, Jian-Ping,Li, Hong-Xi
supporting information, p. 9201 - 9212 (2020/08/14)
An efficient method for visible-light-initiated, nickel-catalyzed Sonogashira C(sp)-C(sp2) coupling has been developed via an energy-transfer mode. Thioxanthen-9-one as a photosensitizer could significantly accelerate the arylation of alkynes with a wide
A transition metal catalytic nitro aromatic hydrocarbon with the end aryl alkyne cross-coupling for preparing aromatic of alkynes (by machine translation)
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Paragraph 0027; 0054; 0056; 0057; 0058, (2018/10/19)
The invention disclosed a kind of transition metal catalytic nitro aromatic hydrocarbon with the end aryl alkyne cross-coupling for preparing aromatic alkyne of the method, the method is under protective atmosphere, nitro aromatic aryl alkyne in the tail end of the palladium-containing catalyst, copper-containing catalyst, phosphine and an amine ligand solution system in the cross-coupling reaction, to obtain the aromatic alkyne product. The synthetic method is cheap and easy to materials and the polarity of the nitro arene as electrophilic reagent synthetic aromatic alkyne, can make up for the deficiency of the traditional Sonogashira coupling of the series, has the following advantages: (1) can avoid using the difficult preparation of the more expensive halogenated hydrocarbon; (2) when the multi-coupling reaction, the polarity of nitro can be a coupling product with the raw materials and the by-product with different polarity easily through the column chromatography separation; (3) adopts the transition metal homogeneous catalysis, is expected to be carried out smoothly under mild conditions, functional group tolerance range is wide. (by machine translation)
Cross-coupling reactions using porous multipod Cu2O microcrystals as recoverable catalyst in aqueous media
Tang, Lin,Wu, Chaoting,Hu, Qiyan,Li, Qian,Zhang, Wu
, (2017/09/06)
Porous multipod Cu2O microcrystals were found to be an efficient, highly recyclable and eco-friendly catalyst for the cross-coupling reactions of aryl halides and terminal alkynes with high yields in aqueous media. Noteworthy, the Cu2O catalyst can be reused for several times without significant decrease in catalytic activity.
A polystyrene supported [PdCl-(SeCSe)] complex: A novel, reusable and robust heterogeneous catalyst for the Sonogashira synthesis of 1,2-disubstituted alkynes and 1,3-enynes
Mohammadi, Elmira,Movassagh, Barahman
supporting information, p. 11471 - 11479 (2018/07/25)
3,5-Bis((phenylselanyl)methyl)phenol has been synthesized as a novel SeCSe pincer type pre-ligand from commercially available 5-hydroxy isophthalic acid through a multistep synthesis. Then, a polystyrene-supported SeCSe pincer ligand and its corresponding palladium complex were prepared and characterized using different techniques including FT-IR, SEM/EDX, TG/DTG, and XPS. The amount of palladium incorporated into the polymer matrix as determined by ICP analysis was obtained to be 3.64 wt% (0.34 mmol g-1). The PS[PdCl-SeCSe] catalytic activity has been evaluated in the Sonogashira coupling of diverse aryl halides with aromatic and aliphatic terminal alkynes. It was also noted that less reactive and inexpensive aryl bromides and aryl chlorides have been successfully cross-coupled with terminal alkynes using low catalyst loading. Moreover, the developed methodology is effective for the stereoselective preparation of substituted 1,3-enynes.
DBU-Mediated Efficient Synthesis of Diaryl Ethynes and Enynes from 1,1-Dibromoalkenes at Room Temperature
Thummala, Yadagiri,Morri, Ashok K.,Karunakar, Galla V.,Doddi, Venkata Ramana
supporting information, p. 6280 - 6285 (2018/11/23)
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
Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes
Qian, Liang-Wei,Sun, Mengli,Dong, Jianyu,Xu, Qing,Zhou, Yongbo,Yin, Shuang-Feng
supporting information, p. 6764 - 6769 (2017/07/15)
A palladium-catalyzed Sonogashira-type coupling between arylsulfonyl hydrazides and terminal alkynes via Ar(C)-S bond cleavage is disclosed, which enables the general synthesis of functionalized internal alkynes, especially the Br-substituted ones, in good to excellent yields under acid- and base-free conditions.
Formation of C-C, C-S and C-N bonds catalysed by supported copper nanoparticles
Mitrofanov, Alexander Yu.,Murashkina, Arina V.,Martín-García, Iris,Alonso, Francisco,Beletskaya, Irina P.
, p. 4401 - 4412 (2017/10/13)
Transition-metal catalysed cross-coupling reactions are still dominated by palladium chemistry. Within the recent past, copper has gained ground against palladium by virtue of its cheaper price and equivalent function in certain reactions. Four catalysts consisting of copper nanoparticles on zeolite, titania, montmorillonite and activated carbon have been tested in three palladium- and ligand-free cross-coupling reactions to form carbon-carbon, carbon-sulfur and carbon-nitrogen bonds. CuNPs/zeolite has been found to be the best one in the Sonogashira reaction of aryl iodides and arylacetylenes, as well as in the coupling of aryl halides with aryl and alkyl thiols, being reusable in both cases. However, the arylation of nitrogen-containing heterocycles (imidazole, pyrazole, benzimidazole and indole) has been better accomplished with CuNPs/titania, albeit CuNPs/activated carbon showed better recycling properties. The catalytic activity of the nanostructured catalysts has been compared with that of twelve commercial copper catalysts, with the former outperforming the latter in the three types of reactions studied.
Using Anilines as Masked Cross-Coupling Partners: Design of a Telescoped Three-Step Flow Diazotization, Iododediazotization, Cross-Coupling Process
Teci, Matthieu,Tilley, Michael,McGuire, Michael A.,Organ, Michael G.
, p. 17407 - 17415 (2016/11/23)
The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three-reactor flow diazotization/iododediazotization/cross-coupling process. The segmented flow stream created by off-gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous-flow unit controlled by custom software created in-house. The resultant aryl iodide was then combined with a stream of cross-coupling solution that fed into the final reactor. The system proved versatile as modifications to the diazotization/iododediazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki–Miyaura and Sonogashira cross-coupled products.
