10229-53-5Relevant academic research and scientific papers
Imine exchange in O-aryl and O-alkyl oximes as a base reaction for aqueous 'dynamic' combinatorial libraries. A kinetic and thermodynamic study
Polyakov, Vladimir A.,Nelen, Marina I.,Nazarpack-Kandlousy, Noureddin,Ryabov, Alexander D.,Eliseev, Alexey V.
, p. 357 - 363 (1999)
Kinetics and mechanisms of the imine exchange reactions of O-alkyl and O-aryl oximes with O-alkyl-and O-aryloxyamines, respectively, were studied by 1H NMR spectroscopy in aqueous solutions. The reaction between benzaldehyde O-methyloxime and O-ethylhydroxylamine at 60 °C is first order in both oxime and the alkoxylamine (the second-order rate constant k2 = 0.86 ± 0.081 mol-1 min-1 at pD 2.9). the reaction being subject to acidic catalysis. A similar imine transfer was studied in the reaction of 1,3-diaminooxyprog with bifunctional oximes. Testing of various additives as potential catalysts for the reaction revealed imidazole as a moderately effective catalyst. The exchange in O-aryl oximes was studied in the interaction between 3-pyridinealdehyde O-pnenyloxime and O-(p-nitrophenyl)hydroxylamine. The reaction is first order in the oxime, but its is independent on the aryloxyamine concentration and pD. The proposed mechanism involves a rate-limiting hydration of the oxime molecule. Mechanisms of the exchange reactions are discussed in relation to their possible use to generate diverse pools of compounds for the recently proposed 'dynamic' combinatorial chemistry approach Copyright
One-pot synthesis of oxime ethers from benzaldehyde or acetophenone, hydroxylamine salt, potassium hydroxide, and alkyl halides
Li, Chunbao,Zhang, Hang,Cui, Yi,Zhang, Shuanming,Zhao, Zheyuan,Choi, Michael C. K.,Chan, Albert S. C.
, p. 543 - 546 (2003)
Oxime ethers were synthesized in one-pot reaction from benzaldehyde or acetophenone, hydroxylamine hydrogen chloride, alkyl halides and KOH in aqueous DMSO. The reactions were completed in 15-50 min with yields in 80-96%.
Change of Orientation in Electrophilic Substitution of Benzaldehydes by O-Alkyloximation Derivatives
Goda, Hiroshi,Ihara, Hirotaka,Hirayama, Chuichi,Sato, Makoto
, p. 1565 - 1568 (1994)
By the introduction of O-alkyloxyimino group, orientation in electrophilic substitution of benzaldehyde can be selectively controlled.
Compound and application thereof
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Paragraph 0151; 0153-0155, (2021/10/05)
The compound has the structure shown in the formula (I) or the formula (II) and R. 1 Selected from H. Deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxy, C1 - C20 chain alkyl, C3 - C20 cycloalkyl, C1 - C20 alkoxy, substituted or unsubstituted C6 - C60 aryl, substituted or unsubstituted C3 - C60 heteroaryl, and the heteroatom in the heteroaryl is selected from O or S. L Is one selected from a single bond, a substituted or unsubstituted C6 - C60 arylene group, a substituted or unsubstituted C3 - C60 heteroarylene group. R Is one selected from H, deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxy, C1 - C20 chain alkyl, C3 - C20 cycloalkyl, C1 - C20 alkoxy, substituted or unsubstituted C6 - C60 aryl, substituted or unsubstituted C3 - C60 heteroaryl. Ar Is a substituted or unsubstituted C6 - C60 aryl group, a substituted or unsubstituted C3 - C60 heteroaryl group. When the compound is applied OLED devices, the device efficiency can be effectively improved, the driving voltage is reduced, and the compound is a good-performance electronic transmission material.
A Short Total Synthesis of Benzophenanthridine Alkaloids via a Rhodium(III)-Catalyzed C-H Ring-Opening Reaction
Aravindan, Narasingan,Jeganmohan, Masilamani
, p. 14826 - 14843 (2021/10/20)
The biologically important naturally available benzophenanthridines were prepared efficiently in three steps with overall good yields. A new synthetic methodology involving a rhodium(III) catalyzed redox-neutral ring-opening of 7-azabenzonorbornadienes with aromatic aldoximes is developed to synthesize the target molecules. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional group substituted aromatic aldoximes as well as substituted 7-azabenzonorbornadienes. The ring-opening products were transformed into highly sensitive 13,14-dehydrobenzo phenanthridine derivatives by HCl hydrolysis. Subsequently, 13,14-dehydrobenzophenanthridines were converted into biologically important benzophenanthridine alkaloids in the presence of DDQ. A possible reaction mechanism was proposed for the C-H ring-opening reaction and supported by the deuterium labeling studies.
Nickel-Catalyzed Transformation of Alkene-Tethered Oxime Ethers to Nitriles by a Traceless Directing Group Strategy
Takahashi, Yoshiyuki,Tsuji, Hiroaki,Kawatsura, Motoi
, p. 2654 - 2665 (2020/02/04)
Nickel-catalyzed transformation of alkene-tethered oxime ethers to nitriles using a traceless directing group strategy has been developed. A series of alkene-tethered oxime ethers derived from benzaldehyde and cinnamyl aldehyde derivatives were converted into the corresponding benzonitriles and cinnamonitriles in 46-98% yields using the nickel catalyst system. Control experiments showed that the alkene group tethered to an oxygen atom on the oximes via one methylene unit plays a key role as a traceless directing group during the catalysis.
Nitrate promoted mild and versatile Pd-catalysed C(sp2)-H oxidation with carboxylic acids
Hao, Hong-Yan,He, Yu-Ting,Lou, Shao-Jie,Luo, Gen,Mao, Yang-Jie,Xiong, Xue,Xu, Dan-Qian,Xu, Zhen-Yuan
supporting information, p. 6732 - 6737 (2020/09/21)
A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.
Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes
Burton, Paul M.,Cooper, Alasdair K.,Nelson, David J.
, p. 565 - 573 (2020/02/13)
A detailed comparison of the effect of coordinating functional groups on the performance of Suzuki-Miyaura reactions catalysed by nickel and palladium is reported, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has effects on cross-coupling reactions that range from a slight improvement in yield to the complete cessation of the reaction. In contrast, palladium does not interact sufficiently strongly with these functional groups to induce selectivity in cross-coupling reactions; the selectivity of palladium-catalysed cross-coupling reactions is predominantly governed by aryl halide electronic properties.
Palladium-catalyzed C-H activation/C-C cross-coupling reactions: Via electrochemistry
Ma, Cong,Zhao, Chuan-Qi,Li, Yi-Qian,Zhang, Li-Pu,Xu, Xue-Tao,Zhang, Kun,Mei, Tian-Sheng
supporting information, p. 12189 - 12192 (2017/11/16)
Palladium-catalyzed C-H activation/C-C cross-coupling reactions typically require stoichiometric chemical oxidants and exogenous ligands. However, there are significant disadvantages associated with the use of traditional stoichiometric oxidants. To overcome these issues, we have developed an electrochemical strategy to achieve methylation and acylation.
Synthesis of 2-fluorocholine aryl carbonyl compounds
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Paragraph 0100, (2017/02/09)
The invention provides a method for synthesizing 2-fluoroarylcarbonyl compounds, which comprises the following steps: converting arylcarbonyl compounds into corresponding carbonyl oxime ether compounds, mildly implementing aryl hydrocarbon chain direct fluoridation of high-selectivity oximido substituent group ortho-position in the presence of a palladium catalyst, a fluoridation reagent and additives, and finally, rehydrolyzing oxime ethers under the action of acid to obtain the 2-fluoroarylcarbonyl compounds. The fluoridation method has the advantages of mild reaction conditions, high substrate adaptability, high fluoridation selectivity and the like, is simple to operate, and has higher application research value.
