13141-36-1Relevant academic research and scientific papers
Methionine: A green and efficient promoter for copper-catalyzed Sonogashira cross-coupling reactions
Hajipour, Abdol R.,Mohammadsaleh, Fatemeh
, p. 787 - 792 (2015)
In the presence of amino acids as environmentally friendly ligands, CuI-catalyzed Sonogashira cross-coupling of various aryl halides with phenylacetylene was conducted to afford the corresponding internal alkynes. l-Methionine was found to be useful for t
Efficient catalytic Sonogashira reaction catalysed by modified fibre-palladium(II) complex in air
Wu, Zhi-Chuan,Sun, Yu-Xing,Xu, Mao-Dong,Tao, Ting-Xian
, p. 478 - 481 (2015)
A hydroxylamine modified polypropylene fibre [Pd(II)-AOFs] was synthesised and used to catalyse the Sonogashira reaction between phenylacetylene and iodobenzene. The results showed that highly efficient catalytic activity can be achieved for the cross-coupling reaction. More importantly, the reaction conditions are moderate and do not require inert gas protection. The catalyst could be readily extracted by simple operations and conveniently recycled four times without an obviously significant decrease in activity.
Pd-Catalyzed decarboxylative alkynylation of alkynyl carboxylic acids with arylsulfonyl hydrazides via a desulfinative process
Chang, Sheng,Liu, Ying,Yin, Shu Zhu,Dong, Lin Lin,Wang, Jian Feng
supporting information, p. 5357 - 5362 (2019/04/04)
In the presence of a Pd(ii)/P-ligand catalytic system, decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions. The reported coupling reactions are very practical as they do not require the protection of inert gas or oxygen and are tolerant to many functional groups.
Arylation of Terminal Alkynes by Aryl Iodides Catalyzed by a Parts-per-Million Loading of Palladium Acetate
Hamasaka, Go,Roy, David,Tazawa, Aya,Uozumi, Yasuhiro
, p. 11640 - 11646 (2019/12/02)
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.
Palladium(II) complex for catalyzing sonogashira coupling reactions and a method thereof
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Page/Page column 17, (2017/02/09)
A palladium(II) complex which catalyzes the Sonogashira coupling reaction efficiently under aerobic condition and a method of employing the palladium(II) complex to synthesize internal alkynes. The palladium(II) complex is an effective catalyst for the co
Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions
Ibrahim, Mansur B.,Ali, Bassam El,Malik, Imran,Fettouhi, Mohammed
, p. 554 - 558 (2016/01/20)
A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the p
Supported palladium nanoparticles-catalyzed decarboxylative coupling approaches to aryl alkynes, indoles and pyrrolines synthesis
Reddy, C. Bal,Bharti, Richa,Kumar, Sandeep,Das, Pralay
, p. 71117 - 71121 (2016/08/05)
The polystyrene supported palladium (Pd@PS) nanoparticles (NPs) catalyzed decarboxylative coupling (DC) of arylhalides and alkynyl carboxylic acids was developed for the synthesis of diaryl alkynes. Indole and 3-pyrroline heterocycles were also synthesized from 2-iodo anilines/amino benzocycloheptene bromide and alkynyl carboxylic acids, following a domino decarboxylative coupling-cyclization (DCC) approach under the same catalytic conditions. The combined anchoring and catalytic behaviour of Pd@PS makes the process favourable for the product formation.
Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons
Xu, Wei,Yu, Bo,Sun, Huaming,Zhang, Guofang,Zhang, Weiqiang,Gao, Ziwei
, p. 353 - 356 (2015/06/02)
Copper-catalyzed Sonogashira-type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5mol% Cu 5mol%), broad reaction scope a
Organocatalytic synthesis of alkynes
Zhang, Mengnan,Jia, Tiezheng,Wang, Carol Y.,Walsh, Patrick J.
supporting information, p. 10346 - 10350 (2015/09/01)
Carbon-carbon triple bonds of alkynes are ubiquitous. They serve as valuable starting materials that can be transformed into a vast array of diverse materials, with applications ranging from medicinal chemistry to electronic materials. The methods used to prepare alkynes involve stoichiometric reactions and the most popular install only a single carbon rather than uniting larger fragments. These methods are useful, but they are limited by harsh conditions or the need to prepare reagents. Introduced herein is the first catalytic method to prepare carbon-carbon triple bonds from precursors that do not contain such linkages. By coupling benzaldehyde and benzyl chloride derivatives under basic conditions with an organocatalyst, good yields of alkynes are obtained. The catalyst, a highly reactive sulfenate anion, is readily generated under the reaction conditions from air-stable precursors. This method represents an attractive organocatalytic alternative to well-established stoichiometric approaches to alkynes and to transition-metal-based alkyne functionalization methods in various applications.
Strategies to reduce hERG K+ channel blockade. Exploring heteroaromaticity and rigidity in novel pyridine analogues of dofetilide
Carvalho, Jo?o F. S.,Louvel, Julien,Doornbos, Maarten L. J.,Klaasse, Elisabeth,Yu, Zhiyi,Brussee, Johannes,Ijzerman, Adriaan P.
supporting information, p. 2828 - 2840 (2013/05/22)
Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG
