31145-10-5Relevant academic research and scientific papers
Palladium Loaded Dendronized Polymer as Efficient Polymeric Sustainable Catalyst for Heck Coupling Reaction
Hiba, K.,Krishna, G. Anjali,Prathapan, S.,Sreekumar, K.
, (2021/08/18)
The palladium incorporated amine-functionalized dendronized polymer was synthesized by the addition of palladium acetate to dendronized polymer in methanol at room temperature. Palladium species are immobilized onto the dendritic structure by their coordination with amino functional groups. The newly developed dendritic system showed high palladium content in the low generation level itself, which was found to be 4.19?mmol/g. This was fairly higher than, the other palladium-based catalysts. Energy dispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, UV–Visible spectroscopy, and X-ray photoelectron spectroscopy were used to confirm the successful synthesis of the new catalyst. It was used as a homogeneous palladium catalyst for Heck coupling reaction between olefins and differently substituted aryl halides and the products were isolated in high yield. The products isolated were in trans configuration, which indicated the selectivity of the newly developed catalytic system. Also, this catalyst system was reused up to nine times without a significant decrease in its catalytic activity. The easy accessibility of catalytic sites, stability, resistance to metal leaching, high catalytic activity and remarkable stereoselectivity with a low amount of catalyst are all due to the dendritic support. The docking study was carried out for all the stilbene derivatives obtained by the Heck coupling reaction against DprE1 protein to study its potential antitubercular activity. All the compounds displayed superior docking score values over the range ??6.5 to ??8.2?kcal/mol, compared to the standard drug isoniazid with docking score of ??6.1?kcal/mol against DprE1. Graphic Abstract: [Figure not available: see fulltext.]
Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction
Yamamoto, Yuki,Kawaguchi, Shin-Ichi,Nishimura, Misaki,Sato, Yuki,Shimada, Yoshihisa,Tabuchi, Akihiro,Nomoto, Akihiro,Ogawa, Akiya
, p. 14684 - 14696 (2020/11/30)
This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.
Palladium schiff base complex immobilized on magnetic nanoparticles: An efficient and recyclable catalyst for Mizoroki and Matsuda-Heck coupling
Vibhute, Sandip P.,Mhaldar, Pradeep M.,Shejwal, Rajendra V.,Rashinkar, Gajanan S.,Pore, Dattaprasad M.
supporting information, (2020/03/23)
The present work elucidates the catalytic efficiency of palladium Schiff base complex immobilized on amine functionalized magnetic nanoparticles for Heck coupling of structurally different aryl halide/arenediazonium tetrafluoroborate with styrene/acrylate/acrylonitrile. Matsuda-Heck coupling proceeds in aqueous media at room temperature whereas Mizoroki-Heck coupling was carried out at 80 °C. Both reactions were successfully furnished with low catalyst loading. The catalyst was easily separated from reaction mixture and reused up to six times without significant loss of catalytic activity.
PdII Immobilized on Ferromagnetic Multi-Walled Carbon Nanotubes Functionalized by Aminated 2-Chloroethylphosphonic Acid with S -Methylisothiourea (FMMWCNTs@CPA@SMTU@PdII NPs) Applied as a Highly Efficient and Recyclable Nanostructured Catalyst for Suzuki-Miyaura and Mizoroki-Heck Cross-Coupling Reactions in Solvent-Free Conditions
Ghasemzadeh, Maryam Sadat,Akhlaghinia, Batool
, p. 674 - 692 (2019/07/12)
The new ferromagnetic nanostructured FMMWCNTs@CPA@SMTU@PdII NPs (IV) as an eco-friendly heterogeneous nanocatalyst with a particle size of ～20-30 nm reported earlier by our group has been found to be very effective for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions at ambient temperature. The procedure has been applied for a wide range of aryl halides, arylboronic acids, and alkenes. The magnetic separation by an external magnetic field, mild reaction conditions, and catalyst reusability up to four times without significant decrease in catalytic activity (reduced catalytic activity from 11 to 18 % in the fifth, sixth, and seventh cycles) made the present method sustainable and economically viable for C-C cross-coupling reactions.
One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
Ding, Weijie,Hu, Juan,Jin, Huile,Yu, Xiaochun,Wang, Shun
, p. 107 - 118 (2017/09/28)
A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.
Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source
Yan, Yiyan,Xu, Xiaohe,Jie, Xiaokang,Cheng, Jingya,Bai, Renren,Shuai, Qi,Xie, Yuanyuan
supporting information, p. 2793 - 2796 (2018/06/25)
The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.
Synthesis of olefins via a Wittig reaction mediated by triphenylarsine
Li, Lun,Stimac, Jared C.,Geary, Laina M.
supporting information, p. 1379 - 1381 (2017/03/17)
An arsine-mediated Wittig reaction for the synthesis of olefins is described. After heating triphenylarsine in the presence of an activated alkyl bromide for 30?min, the resulting arsonium salt condensed with aldehydes in as little as 5?min at room temperature, yielding the olefins in high yields. Aromatic, heteroaromatic, and alkyl aldehydes were all suitable substrates for this process.
CUCN-MEDIATED ONE POT PRODUCTION OF CINNAMONITRILE DERIVATIVES
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Paragraph 0046 - 0048; 0055, (2015/02/19)
The present invention discloses a cheaper and practical protocol for the construction of a wide variety of o-cyanocin-namonitrile and their structural analogues that proceeds with good yields in a single step using CuCN as the only reagent.
N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley-Griffith (TPAP) tandem oxidation-Wittig reactions
Read, Christopher D. G.,Moore, Peter W.,Williams, Craig M.
supporting information, p. 4537 - 4540 (2015/09/15)
N,N,N′,N′-Tetramethylethylenediamine dioxide (TMEDAO2) was explored as a more atom economical co-oxidant for the Ley-Griffith oxidation of alcohols to aldehydes. TMEDAO2 was found to selectivity oxidise benzylic and allylic alcohols in comparable yields to that of the standard Ley-Griffith co-oxidant (NMO). Importantly TMEDAO2 facilitated tandem Ley-Griffith-Wittig reactions with stabilised ylides, in good to excellent yields, without the requirement of anhydrous conditions.
Cu-catalyzed debrominative cyanation of gem-dibromoolefins: A facile access to α,β-unsaturated nitriles
Ahuja, Brij Bhushan,Sudalai, Arumugam
, p. 5918 - 5923 (2015/06/02)
An efficient catalytic route for the synthesis of α,β-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed. The method utilized inexpensive reagents such as Cu2O as a catalyst, l-proline as a ligand and NaCN as a cyanide source to afford α,β-unsaturated nitriles in high yields (62-86%). A deuterium exchange study has shown that one of the bromide atoms of gem-dibromoolefins exchanges with cyanide while the other with a deuterium atom.
