40327-51-3Relevant academic research and scientific papers
A high-yielding protocol for the synthesis of 4,5-diarylpyrimidin-2-amine derivatives from chalcones
Kooramatom Unni, Krishnaraj,Menon, Prasanth K.,George, Scholly Clair,Thomas, Sajesh P.,Devaky
, p. 112 - 118 (2021/10/07)
A novel, high yielding and versatile protocol was achieved for the synthesis of 4,5-diaryl-2-pyrimidinamine derivatives from chalcones. The synthesis was accomplished by converting the chalcones into 3-chloro-2,3-diaryl-2-propen-1-ones followed by subsequent reaction with amidine derivatives.
Asymmetric epoxidation of α,β-unsaturated ketones via an amine-thiourea dual activation catalysis
Zhang, Lu-Wen,Wang, Li,Ji, Nan,Dai, Si-Yang,He, Wei
supporting information, (2021/03/15)
A simple asymmetric epoxidation method is developed to effectively synthesize chiral α-carbonyl epoxides through an amine-thiourea dual activation catalysis. In this method, TBHP, as an oxidant, determined the reaction rate, and the chiral amine-thiourea catalyst effectively controlled the stereoselectivity of the reaction, and KOH promoted deprotonation. 22 examples of α,β-unsaturated ketones with various substituent groups are smoothly converted into α-carbonyl epoxides with moderate to excellent enantiomeric excess.
Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe3)2]3with chiral TADDOL ligands
Shan, Haiwen,Lu, Chengrong,Zhao, Bei,Yao, Yingming
, p. 1043 - 1053 (2021/01/25)
The catalytic asymmetric epoxidation of α,β-unsaturated ketones by tert-butylhydroperoxide (TBHP) has been well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = La(1), Nd(2), Sm(3), Y(4), Yb(5)) with chiral TADDOL ligands. It was found that
Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
Jurczak, Janusz,Majdecki, Maciej,Tyszka-Gumkowska, Agata
supporting information, (2020/11/13)
A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.
Ligand regulation for manganese-catalyzed enantioselective epoxidation of olefins without acid
Xu, Daqian,Sun, Qiangsheng,Lin, Jin,Sun, Wei
supporting information, p. 13101 - 13104 (2020/11/09)
A novel manganese catalyst bearing an l-proline-derived N4 ligand has been developed for enabling acid-free asymmetric epoxidation of olefins with tert-butyl hydroperoxide as the oxidant. A variety of olefins that are well-matched in size with the ligand
Method for preparing epoxide by one-pot olefin aerobic epoxidation
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Paragraph 0054-0055, (2020/01/03)
The invention relates to a method for preparing an epoxide by one-pot olefin aerobic epoxidation, and belongs to the technical field of organic synthesis. An olefin, an alkyl aromatic compound and analkali are added into a solvent, or an olefin, an alkyl aromatic compound and an alkali are directly mixed; the temperature is raised to 70-160 DEG C in an air or oxygen atmosphere; reacting is carried out for 1-48 hours; and the olefin is directly oxidized into the corresponding epoxide in the presence of the alkyl aromatic compound, the alkali and air (or oxygen), wherein the yield is up to 99%.In the reaction process, the generated alkyl peroxide is generated in situ and consumed in situ, so that the concentration of the alkyl peroxide is kept at a lower level; and generated alkyl peroxy free radicals can also react with the olefin to further generate the peroxide, and efficiency is improved. The method has the advantages of simple operation, mild conditions, low raw material cost andno need of special complex equipment, and has a good industrial application prospect.
Chiral calcium-catalyzed asymmetric epoxidation reactions using hydrogen peroxide as the terminal oxidant
Yamashita, Yasuhiro,Macor, Joseph Alexander,Fushimi, Seiya,Tsubogo, Tetsu,Kobayashi, Shū
, p. 847 - 850 (2018/09/10)
Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivitie
Syntheses, Structures, and Catalytic Activities of the Anionic Heterobimetallic Rare-Earth Metal Complexes Supported by Pyrrolyl-Substituted 1,2-Diimino Ligands
Wang, Wei,Wang, Xiaojia,Zhou, Shuangliu,Xu, Xiaolong,Du, Jun,Zhang, Lijun,Mu, Xiaolong,Wei, Yun,Zhu, Xiancui,Wang, Shaowu
supporting information, p. 10390 - 10400 (2018/08/28)
A series of the anionic heterobimetallic rare-earth metal complexes supported by trans- or chiral pyrrolyl-substituted 1,2-diimino ligands were synthesized in good yields via reactions of [(Me3Si)2N]3RE(μ-Cl)Li(THF)3
Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines
Wu, Yufeng,Zhou, Guangli,Meng, Qingwei,Tang, Xiaofei,Liu, Guangzhi,Yin, Hang,Zhao, Jingnan,Yang, Fan,Yu, Zongyi,Luo, Yi
, p. 13051 - 13062 (2018/10/25)
An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H2TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.
Visible-Light-Driven Epoxyacylation and Hydroacylation of Olefins Using Methylene Blue/Persulfate System in Water
De Souza, Gabriela F. P.,Bonacin, Juliano A.,Salles, Airton G.
, p. 8331 - 8340 (2018/07/21)
A visible-light-driven strategy for hydroacylation and epoxyacylation of olefins in water using methylene blue as photoredox catalyst and persulfate as oxidant is reported. In this unprecedented unified approach, two different transformations are accomplished using only one set of reagents. The method has a broad scope spanning a range of aromatic and aliphatic aldehydes as well as conjugated and nonconjugated olefins to deliver ketones and epoxyketones from abundant and inexpensive chemical feedstocks.
