100752-58-7Relevant academic research and scientific papers
Nickel (II) dibenzotetramethyltetraaza[14]annulene supported on DFNS nanoparticles catalyst in carbonylative sonogashira coupling
Mohsen Sadeghzadeh, Seyed,Tian, Shaopeng,Yang, Qianqian
, (2021)
In this study, the carbonylative sonogashira coupling reaction was performed in the presence of CO (2 MPa) and Nitmtaa?DFNS as NPs. Nickel(II)dibenzotetramethyltetraaza[14]annulene complex (Nitmtaa) prepared and immobilized on amino-fucntionnalized DFNS (N-DFNS) via Ni[sbnd]N (NH2) bond to obtain a stable and reusable new nanocatalyst named as Nitmtaa?DFNS. Good to superb performance products were provided deploying Nitmtaa?DFNS nanocatalyst. In addition, the anatomy of Nitmtaa?DFNS has been distinguished by various methods, including XRD, VSM, FT-IR, SEM, EDX, TEM, and TGA. In addition, the hot filtration test provided complete insight into the heterogeneity of the catalyst. The reuse and recycling of the catalyst were repeatedly investigated for coupling reactions. In addition, the mechanism of the coupling reactions was thoroughly studied.
Palladium anchored on amine-functionalized K10 as an efficient, heterogeneous and reusable catalyst for carbonylative Sonogashira reaction
Chavan, Sujit P.,Varadwaj, G.Bishwa Bidita,Parida, Kulamani,Bhanage, Bhalchandra M.
, p. 237 - 245 (2015)
The present work describes the immobilization of palladium chloride (II) on the amine functionalized K10 support and its application toward the carbonylative Sonogashira reactions. The various catalyst characterization techniques revealed the successful grafting of APTES moiety on the K10 clay surface through covalent bonding and Pd with the NH2 groups of APTES@K10 through co-ordinate bonding. The immobilized catalyst was successively applied for copper and phosphine free carbonylative Sonogashira reaction of aryl and hetero aryl iodides with terminal alkynes. To our delight, the electron withdrawing aryl halides can be efficiently utilized as an electrophiles giving higher selectivity toward carbonylated products. Moreover, dibenzoylmethane which is a potential synthetic intermediate in organic transformation has been also synthesized using this protocol. Recovery of catalyst by simple filtration and its reuse up to four consecutive cycles ensure the robustness of present catalytic protocol.
Palladium-catalyzed chemoselective cross-coupling of acyl chlorides and organostannanes
Lerebours, Rachel,Camacho-Soto, Alexandra,Wolf, Christian
, p. 8601 - 8604 (2005)
Chemoselective cross-coupling of aliphatic and aromatic acyl chlorides with aryl-, heteroaryl-, and alkynylstannanes proceeds in up to 98% yield using 2.5 mol % of bis(di-tert-butylchlorophosphine)palladium(II) dichloride as the precatalyst. Various functional groups including aryl chlorides and bromides that usually undergo oxidative addition to palladium complexes bearing phosphinous acid or dialkylchlorophosphine ligands are tolerated. This procedure allows convenient ketone formation and eliminates inherent limitations of Friedel-Crafts acylations such as substituent-directing effects and typical reactivity requirements of Lewis acid-catalyzed electrophilic aromatic substitutions.
Palladium chloride-cryptand-22 complex: An efficient catalyst for the copper-, phosphorus-, and solvent-free synthesis of ynones
Navidi, Mozhgan,Movassagh, Barahman
, p. 1363 - 1367 (2013)
The palladium chloride-cryptand-22 complex was found to be an efficient catalyst for the copper-, phosphorus-, and solvent-free coupling reaction of terminal alkynes with different acyl chlorides in the presence of triethylamine as base, at room temperatu
Application of phase-vanishing method with CO gas evolution to carbonylation reactions
Adachi, Yusuke,Matsubara, Hiroshi
, p. 89 - 95 (2018)
Although carbon monoxide (CO) is considered a practical source of the carbonyl functionality in various compounds, handling CO gas is difficult. The phase-vanishing (PV) method, using highly fluorinated solvents as the phase screen, was thus employed, in which CO was evolved for use in organic synthesis. An H-shaped reactor bearing two reaction chambers was employed. In the first chamber, CO was efficiently generated from sulfuric acid and ammonium formate under the PV conditions, and then consumed in the second chamber in a range of palladium-catalysed carbonylation reactions, affording the desired products. Use of this PV system allowed for easy and safe generation of hazardous CO gas, and its use thereof in organic synthesis.
One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization
Thirukovela, Narasimha Swamy,Balaboina, Ramesh,Botla, Vinayak,Vadde, Ravinder,Jonnalagadda, Sreekantha Babu,Vasam, Chandra Sekhar
, p. 6471 - 6481 (2019)
Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.
Palladium- and solvent-free synthesis of ynones by copper(I)-catalyzed acylation of terminal alkynes with acyl chlorides under aerobic conditions
Mohammadi, Elmira,Movassagh, Barahman,Navidi, Mozhgan
, p. 70 - 75 (2014)
Air-stable CuI/cryptand-22 complex was found to be a highly active catalyst for the solvent-free cross-coupling reaction of terminal alkynes with different acyl chlorides in the presence of Et3N as base to give the corresponding ynon
Nickel catalysed carbonylative Sonogashira reaction for the synthesis of diarylalkynones and 2-substituted flavones
Charugandla, Renuka,Vangala, Markandeya Sarma,Chidara, Sridhar,Korupolu, Raghu Babu
, p. 3283 - 3287 (2018)
The nickel catalyzed, palladium/phosphine free carbonylative Sonogashira reaction of terminal alkynes with substituted aryl and heteroaryl iodides is described. This protocol provides mild and robust conditions to synthesize a variety of substituted aryl α,β-alkynyl ketones and flavones in good to excellent isolated yields. This methodology tolerates several functional groups such as electron donating (methyl, isopropyl, tert-butyl, methoxy) as well as electron withdrawing (trifluoromethyl, nitro, esters, nitrile) groups on the terminal alkynes and iodides.
Carbonylative Sonogashira Coupling of Aryl Iodides with Terminal Alkynes Catalyzed by Palladium Nanoparticles
Feng, Xiujuan,Song, Jiliang,Bao, Ming
, p. 337 - 345 (2018)
A convenient and efficient method for the synthesis of α,β-alkynyl ketones from the three-component coupling of aryl iodides, terminal alkynes, and carbon monoxide (carbonylative Sonogashira coupling reaction) is successfully developed. The carbonylative Sonogashira coupling reaction proceeded smoothly under mild conditions in the presence of palladium nanoparticles to produce the corresponding α,β-alkynyl ketones in good to excellent yields.
Oxidative Coupling of Terminal Alkynes with Aldehydes Leading to Alkynyl Ketones by Using Indium(III) Bromide
Ogiwara, Yohei,Kubota, Masahito,Kurogi, Kotaro,Konakahara, Takeo,Sakai, Norio
, p. 18598 - 18600 (2015)
An indium(III)-promoted direct acylation of terminal alkynes using aldehydes leading to ynones was developed. In contrast to the previous addition reactions of alkynes to aldehydes, which provide propargylic alcohols, the oxidative coupling proceeded exclusively to afford alkynyl ketones. The products were likely generated through an Oppenauer oxidation of the indium propargylic alkoxide species by excess amounts of aldehydes.
