95827-00-2Relevant academic research and scientific papers
Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes
Fu, Xiao-Yang,Si, Ya-Feng,Qiao, Li-Peng,Zhao, Yu-Fen,Chen, Xiao-Lan,Yu, Bing
supporting information, p. 574 - 580 (2021/11/13)
A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.
Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
supporting information, (2021/05/31)
A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems
Apolinar, Omar,Derosa, Joseph,Engle, Keary M.,Karunananda, Malkanthi K.,Kleinmans, Roman,Li, Zi-Qi,Tran, Van T.,Wisniewski, Steven R.
supporting information, p. 5311 - 5316 (2021/07/26)
A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.
Electrochemical Chalcogenation of β,γ-Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines
Baidya, Mrinmay,De Sarkar, Suman,Mahanty, Kingshuk,Maiti, Debabrata,Mallick, Samrat
supporting information, (2020/02/04)
The current report represents a transition-metal-free synthesis of oxazoline and isoxazoline derivatives by a tandem electro-oxidative chalcogenation-cyclization process. Both C?Se and C?S bond-forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline derivatives were synthesized with up to 91% isolated yield. (Figure presented.).
Enantioselective Synthesis of Isoxazolines Enabled by Palladium-Catalyzed Carboetherification of Alkenyl Oximes
Chen, Mingjie,Li, Wenbo,Wang, Lei,Wang, Yuzhuo,Zhang, Junliang,Zhang, Kenan
supporting information, p. 4421 - 4427 (2020/02/11)
Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields with u
Copper-catalyzed asymmetric cyanation of alkenes via carbonyl-assisted coupling of alkyl-substituted carbon-centered radicals
Zhou, Song,Zhang, Guoyu,Fu, Liang,Chen, Pinhong,Li, Yibiao,Liu, Guosheng
supporting information, p. 6299 - 6303 (2020/10/02)
Based on a copper-catalyzed radical relay strategy, the first copper-catalyzed asymmetric cyanation of alkyl-substituted alkenes has been developed. The reaction, featuring mild reaction conditions and excellent functional group compatibilities, provides
Copper-Catalyzed Aerobic Cyclization of β,γ-Unsaturated Hydrazones with Concomitant CC Bond Cleavage
Fan, Zhenwei,Feng, Jiahao,Hou, Yuchen,Rao, Min,Cheng, Jiajia
supporting information, p. 7981 - 7985 (2020/11/02)
A Cu-catalyzed aerobic oxidative cyclization of β,γ-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant CC bond cleavage of β,γ-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible byproducts. The advantages of this reaction include operational simplicity, a broad reaction scope, and a mild selective reaction process.
Copper-Promoted 6- endo-trig Cyclization of β,γ-Unsaturated Hydrazones for the Synthesis of 1,6-Dihydropyridazines
Guo, Yong-Qiang,Zhao, Mi-Na,Ren, Zhi-Hui,Guan, Zheng-Hui
supporting information, p. 3337 - 3340 (2018/06/11)
A novel and efficient strategy for the synthesis of 1,6-dihydropyridazines via copper-promoted 6-endo-trig cyclization of readily available β,γ-unsaturated hydrazones have been developed. A series of 1,6-dihydropyridazines have been synthesized by this method with good yields, high functional group tolerance, and remarkable regioselectivity under mild conditions. Importantly, the 1,6-dihydropyridazines can be efficiently converted to biologically important pyridazines in the presence of NaOH.
Iminoxyl Radical-Promoted Oxycyanation and Aminocyanation of Unactivated Alkenes: Synthesis of Cyano-Featured Isoxazolines and Cyclic Nitrones
Chen, Fei,Zhu, Fei-Fei,Zhang, Man,Liu, Rui-Hua,Yu, Wei,Han, Bing
supporting information, p. 3255 - 3258 (2017/06/23)
A novel and facile approach to vicinal oxycyanation and aminocyanation of internal unactivated alkenes is developed. This method utilizes the dichotomous reactivity of iminoxyl radical derived from the initiation of β,γ- and γ,δ-unsaturated ketoximes to provide the general difunctionalization of internal alkenes using tert-butyl hydroperoxide (TBHP) as the environmentally friendly oxidant, CuCN as the commercially available cyanating reagent, and pentamethyldiethylenetriamine (PMDETA) as the ligand. By using this protocol, a series of useful cyano-featured isoxazolines and cyclic nitrones were efficiently prepared.
Green organocatalytic synthesis of isoxazolines via a one-pot oxidation of allyloximes
Triandafillidi, Ierasia,Kokotos, Christoforos G.
supporting information, p. 106 - 109 (2017/11/27)
A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H2O2 as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated, leading to isoxazolines in moderate to excellent yields.
