349-58-6Relevant academic research and scientific papers
Predicting the hydrolytic breakdown rates of organophosphorus chemical warfare agent simulants using association constants derived from hydrogen bonded complex formation events
Chu, Dominique F.,Clark, Ewan R.,Ellaby, Rebecca J.,Hiscock, Jennifer,Pépés, Antigoni
, (2021/11/22)
Organophosphorus (OP) chemical warfare agents (CWAs) represent an ongoing global threat, through either purposeful environmental release or the need to dispose of historic stockpiles. This presents a need for the development of novel decontamination technologies. Due to the toxic nature and legal limitations placed on OP CWAs, the use of appropriate OP simulants that mimic the reactivity but not the toxicity of the agents themselves is vital to decontamination studies. Herein, we show that association constants derived from non-specific hydrogen bonded complexation events may be used as parameters within models to predict simulant reactivity. We also discuss the limitations that should be placed on such data.
Radical-anion coupling through reagent design: hydroxylation of aryl halides
Chechik, Victor,Greener, Andrew J.,James, Michael J.,Oca?a, Ivan,Owens-Ward, Will,Smith, George,Ubysz, Patrycja,Whitwood, Adrian C.
, p. 14641 - 14646 (2021/11/17)
The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described. Key to the success of this approach was the identification of a reducing oxime anion which can interact and couple with open-shell aryl radicals. Experimental and computational studies support the proposed radical-nucleophilic substitution chain mechanism.
A practical method for preparation of phenols from arylboronic acids catalyzed by iodopovidone in aqueous medium
Dong, Bin,Ke, Yanxiong,Lu, Guangying,Ren, Jiangmeng,Ren, Yaoyao,Zeng, Bu-Bing,Zhou, Bin
, (2019/09/06)
A novel and efficient strategy for the ipso-hydroxylation of arylboronic acids to phenols has been developed using inexpensive, readily available, air-stable water-soluble povidone iodine as catalyst and aqueous hydrogen peroxide as oxidizing agent. The reactions were performed at room temperature under metal-, ligand- and base-free condition in a short reaction time. The corresponding substituted phenols were obtained in moderate to good yields by oxidative hydroxylation of arylboronic acids in aqueous medium.
8-Mercaptoquinoline as a Ligand for Enhancing the Photocatalytic Activity of Pt(II) Coordination Complexes: Reactions and Mechanistic Insights
Casado-Sánchez, Antonio,Uygur, Mustafa,González-Mu?oz, Daniel,Aguilar-Galindo, Fernando,Nova-Fernández, José Luis,Arranz-Plaza, Judith,Díaz-Tendero, Sergio,Cabrera, Silvia,Manche?o, Olga García,Alemán, José
, p. 6437 - 6447 (2019/05/24)
A family of quinoline-platinum(II) complexes as efficient photocatalysts is presented. Their key characteristic is their easy preparation by coordination of the readily available 8-hydroxy- or 8-thio-quinoline ligands, which are well known for their strong chelating ability to different metal ions. In the different photochemical transformations investigated, such as cross-dehydrogenative coupling, oxidation of arylboronic acids, and asymmetric alkylation of aldehydes, 8-mercaptoquinoline-Pt(II) complex proved to be the most general catalyst. Moreover, quenching experiments showed that, contrary to related methods reported in the literature, these complexes followed an oxidative quenching mechanism in all transformations studied. Besides, simulations performed with high-level ab initio methods of the complexes have helped to understand their photocatalytic activity.
A catalytic oxidation fragrant boron class compound preparing phenol method (by machine translation)
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Paragraph 0027; 0051; 0052, (2017/08/08)
The invention discloses a method for catalytic oxidation of phenolic compounds fragrant boron class compound synthesis method, the flux in the solvent in the aqueous solution, under the action of alkali, adding hydrazine hydrate or acid hydrazides catalyst, catalytic oxidation fragrant boron class compound directly for the preparation of phenolic compound. The invention of the method of preparation of the phenol compound, the catalyst is a cheap hydrazine hydrate or hydrazine compound, the oxidizing agent is atmospheric pressure of air or oxygen, the reaction does not need good and activeness metal catalyst, is extensive and stable substrate, substrate-sensitive functional group compatibility good and wide range of application. In the optimized under the reaction conditions, the yield of the target product separation up to 99%. (by machine translation)
Reaction of 1,2-difunctionalized ethanes with aryl iodides in copper-catalyzed cross-coupling: Application to synthesis of phenols
Kim, Jihye,Battsengel, Oyunsaikhan,Liu, Yajun,Chae, Junghyun
supporting information, p. 2833 - 2840 (2016/02/05)
A series of 1,2-difunctionalized ethanes, such as ethylene glycol, 2-aminoethanol, 1,2-diaminoethane, 2-dimethylaminoethanol N',N'-dimethylethane-1,2-diamine, were investigated to test the reactivity with aryl iodides in the presence of copper catalysts. Under the reaction conditions, they produce the various Cheteroatom cross-coupled products. Interestingly, ethylene glycol and 2-dimethylaminoethanol afforded mainly the phenolic compounds while the others produced different cross-coupled products. Although ethylene glycol and 2-dimethylaminoethanol resulted in the same product, their behaviors in the reaction were quite different: ethylene glycol appears to mostly act as the ligand and 2-dimethylaminoethanol appears to serve as both the ligand and reactant. This finding led to a copper-catalyzed synthesis of phenols using either ethylene glycol or 2-dimethylaminoethanol, which can be applied to a variety of aryl iodides, providing an alternative synthetic route to phenols.
Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers
Liu, Yajun,Park, Se Kyung,Xiao, Yan,Chae, Junghyun
supporting information, p. 4747 - 4753 (2014/06/24)
A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is
Continuous-flow synthesis of functionalized phenols by aerobic oxidation of grignard reagents
He, Zhi,Jamison, Timothy F.
supporting information, p. 3353 - 3357 (2014/04/03)
Phenols are important compounds in chemical industry. An economical and green approach to phenol preparation by the direct oxidation of aryl Grignard reagents using compressed air in continuous gas-liquid segmented flow systems is described. The process tolerates a broad range of functional groups, including oxidation-sensitive functionalities such as alkenes, amines, and thioethers. By integrating a benzyne-mediated in-line generation of arylmagnesium intermediates with the aerobic oxidation, a facile three-step, one-flow process, capable of preparing 2-functionalized phenols in a modular fashion, is established. Putting on airs: Aerobic oxidation of (hetero)aryl Grignard reagents using compressed air proceeds with a gas-liquid continuous-flow system, thus enabling preparation of fucntionalized phenols. By integrating an in-line generation of ArMgBr intermediates with the aerobic oxidation, ortho-functionalized phenols can be assembled. The method demonstrates good functional-group (FG) compatibility, mild reaction conditions, and short reaction times.
Copper(II)-catalyzed hydroxylation of aryl halides using glycolic acid as a ligand
Xiao, Yan,Xu, Yongnan,Cheon, Hwan-Sung,Chae, Junghyun
, p. 5804 - 5809 (2013/07/25)
Copper(II)-catalyzed hydroxylation of aryl halides has been developed to afford functionalized phenols. The protocol utilizes the reagent combination of Cu(OH)2, glycolic acid, and NaOH in aqueous DMSO, all of which are cheap, readily available, and easily removable after the reaction. A broad range of aryl iodides and activated aryl bromides were transformed into the corresponding phenols in excellent yields. Moreover, it has been shown that C-O(alkyl)-coupled product, instead of phenol, can be predominantly formed under similar reaction conditions.
Synthesis of phenol, aromatic ether, and benzofuran derivatives by copper-catalyzed hydroxylation of aryl halides
Zhao, Dongbing,Wu, Ningjie,Zhang, Shuai,Xi, Peihua,Su, Xiaoyu,Lan, Jingbo,You, Jingsong
supporting information; experimental part, p. 8729 - 8732 (2010/01/16)
A smooth operator: The copper-catalyzed synthesis of phenols from aryl halides was carried out under relatively mild reaction conditions. Alkyl aryl ethers and benzofurans could also be prepared smoothly by one-pot domino protocols based on hydroxylation of aryl iodides (see scheme).
