54095-43-1Relevant academic research and scientific papers
BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions
Hu, Wenkang,Liu, Hongqiang,Luo, Lan,Wang, Dawei,Zeng, Wei
, (2021/11/16)
Highly active catalysts play an important role in modern catalysis. A novel and efficient ligand benzotriazole-pyrimidine (BTP) and the corresponding rhodium composite on C3N4 were successfully synthesized. The resulting rhodium composite was fully characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), x-ray diffraction (XRD), thermogravimetric analysis (TGA), and x-ray photoelectron spectroscopy (XPS). The obtained composite exhibited good catalytic activity and good recovery performance in the synthesis of quinoxaline from 2-aminobenzyl alcohol and benzonitrile, and more than 20 quinoxalines were obtained in good yields. Additionally, it also showed that rhodium composite could achieved good catalytic performance in the synthesis of functionalized ketone through borrowing hydrogen strategy.
Nickel-catalyzed α-alkylation of ketones with benzyl alcohols
Li, Min,Liu, Jichang,Liu, Ning,Shi, Lei,Wang, Yubin,Wu, Di
, (2021/11/04)
We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.
Direct conversion of secondary propargyl alcohols into 1,3-di-arylpropanoneviaDBU promoted redox isomerization and palladium assisted chemoselective hydrogenation in a single pot operation
Bera, Mrinal K.,Chandra, Shubhadeep,De, Rimpa,Savarimuthu, S. Antony
, p. 17871 - 17877 (2021/10/12)
Palladium(ii)acetate is found to be an efficient catalyst for the single-step conversion of secondary propargyl alcohols to 1,3-diarylpropanone derivatives under mild basic conditions. The reaction is believed to proceedviaredox isomerisation of secondary propargyl alcohols followed by chemoselective reduction of an enone double bond with formic acid as an adequate hydrogen donor. A large number of 1,3-diarylpropanone derivatives may readily be prepared from a milligram to a multigram scale.
Application of 4, 6-dimethyl-2-mercaptopyrimidine bivalent nickel complex in preparation of [alpha]-alkyl ketone
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Paragraph 0034-0035, (2021/04/07)
The invention relates to the field of metal organic chemistry, in particular to application of a 4, 6-dimethyl-2-mercaptopyrimidine bivalent nickel complex in preparation of [alpha]-alkyl ketone, which takes a 4, 6-dimethyl-2-mercaptopyrimidine nickel (II) compound as a catalyst and realizes selective preparation of [alpha]-alkyl ketone through cross-coupling reaction of secondary alcohol and primary alcohol by regulating and controlling reaction conditions. The coupling reaction is carried out in anhydrous toluene in the presence of alkali under the protection of inert gas. The application has the advantages of mild reaction system conditions and wide substrate applicability, and effectively avoids the use of organic phosphine ligands and noble metals.
Ligand-tuned cobalt-containing coordination polymers and applications in water
Tao, Rong,Yang, Yike,Zhu, Haiyan,Hu, Xinyu,Wang, Dawei
supporting information, p. 8452 - 8461 (2020/12/29)
Ligands play a key role in modern catalysis research and occasionally determine whether a reaction will take place under specific conditions, such as in water. In this experiment, ligands containing an indole-based diacid moiety were employed to prepare the corresponding cobalt coordination polymer material (Co-CIA) and porous oval polymer material (Co-NCIA). Interestingly, it was observed that Co-CIA could promote the alkylation of ketones with alcohols and alcohols with alcohols, while Co-NCIA was effective for the synthesis of 1-benzyl-2-aryl-1H-benzo[d]imidazoles from various phenylenediamine and benzyl alcohols through borrowing hydrogen and dehydrogenation strategies. Other mechanism explorations, such as deuterium labeling experiments and a kinetics study, were conducted to better understand Co-CIA and Co-NCIA systems and the related transformations. Our studies provided an efficient method for the development of highly active cobalt coordination polymer materials with excellent recovery performance for dehydrogenation and borrowing hydrogen reactions under water and base-free conditions.
Iodine-catalyzed α,β-dehydrogenation of ketones and aldehydes generating conjugated enones and enals
Cao, Yuanjie,Chen, Tieqiao,Huang, Tianzeng,Liu, Long
supporting information, p. 8697 - 8701 (2020/06/08)
A transition metal-free α,β-dehydrogenation of ketones and aldehydes was developed. This reaction was conducted in a facile I2/KI/DMSO system to produce the corresponding unsaturated compounds in good to high yields. The gram-scale experiment also indicated the potential synthetic value of this new reaction in organic synthesis. In the reaction, DMSO acted as both solvent and mild oxidant.
Preparation method of novel aromatic ketone compound
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Paragraph 0031-0032, (2020/12/08)
The invention discloses a preparation method of a novel aromatic ketone compound. According to the preparation method, an aromatic carboxylic acid compound and an aromatic olefin compound are used asreaction raw materials, triphenylphosphine is taken as a deoxidizing reagent, Methylenene blue is taken as a photocatalyst, stirring and reacting are carried out at room temperature in an N,N-dimethylacetamide solvent under the irradiation of a white light lamp in a nitrogen atmosphere and under the condition of taking 2,4,6-trimethylpyridine as an alkali, thereby obtaining a target product, namely the aromatic ketone compound. The method has the advantages of mild reaction conditions, simplicity in operation, low cost, convenience in purification, environmental friendliness and the like.
Sustainable and Selective Alkylation of Deactivated Secondary Alcohols to Ketones by Non-bifunctional Pincer N-heterocyclic Carbene Manganese
Lan, Xiao-Bing,Ye, Zongren,Liu, Jiahao,Huang, Ming,Shao, Youxiang,Cai, Xiang,Liu, Yan,Ke, Zhuofeng
, p. 2557 - 2563 (2020/05/04)
A sustainable and green route to access diverse functionalized ketones via dehydrogenative–dehydrative cross-coupling of primary and secondary alcohols is demonstrated. This borrowing hydrogen approach employing a pincer N-heterocyclic carbene Mn complex displays high activity and selectivity. A variety of primary and secondary alcohols are well tolerant and result in satisfactory isolated yields. Mechanistic studies suggest that this reaction proceeds via a direct outer-sphere mechanism and the dehydrogenation of the secondary alcohol substrates plays a vital role in the rate-limiting step.
Controlling the selectivity and efficiency of the hydrogen borrowing reaction by switching between rhodium and iridium catalysts
Wang, Danfeng,McBurney, Roy T.,Pernik, Indrek,Messerle, Barbara A.
supporting information, p. 13989 - 13999 (2019/10/01)
The catalytic alkylation of ketones with alcohols via the hydrogen borrowing methodology (HB) has the potential to be a highly efficient approach for forming new carbon-carbon bonds. However, this transformation can result in more than one product being formed. The work reported here utilises bidentate triazole-carbene ligated iridium and rhodium complexes as catalysts for the selective formation of alkylated ketone or alcohol products. Switching from an iridium centre to a rhodium centre in the complex resulted in significant changes in product selectivity. Other factors-base, base loading, solvent and reaction temperature-were also investigated to tune the selectivity further. The optimised conditions were used to demonstrate the scope of the reaction across 17 ketones and 14 alcohols containing a variety of functional groups. A series of mechanistic investigations were performed to probe the reasons behind the product selectivity, including kinetic and deuterium studies.
Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols
Zhang, Meng-Juan,Li, Hong-Xi,Young, David J.,Li, Hai-Yan,Lang, Jian-Ping
supporting information, p. 3567 - 3574 (2019/04/14)
The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.
