877-48-5Relevant academic research and scientific papers
Direct Acetoxylation of Arenes
Hong Nguyen, Thi Anh,Hou, Duen-Ren
supporting information, p. 8127 - 8131 (2021/08/23)
Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.
One-pot process for preparing acetic acid -2, 5 -dimethylphenyl ester and 2,5 -dimethylnitrobenzene (by machine translation)
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Paragraph 0042-0046, (2020/06/16)
The method comprises the following steps of: adding acetic anhydride in a single-mouth flask; adding additional p-xylene; adding the reaction solution obtained in Step III to a separatory funnel; stirring the reaction; cooling to room temperature; and quenching the reaction solution obtained in the step three steps: adding deionized water, stirring the reaction and cooling to room temperature; and quenching the reaction solution in step three steps: adding deionized water, stirring the reaction and cooling to room temperature; and thirdly, distilling the reaction solution obtained in the step three steps into dichloromethane to volatilize to obtain a product, namely acetic acid -2 -2, 5 - 5 -dimethylphenyl ester 2,5 - and 2,5 -dimethylnitrobenzene. To the method, nitrate is used as an oxidant and a nitrate agent, the price is low,2-dimethylnitrobenzene can be obtained while the acetic acid 5 - and 2,5 -dimethylphenyl ester are obtained, two products can be obtained through one-step reaction, and the utilization rate of the raw material is improved. (by machine translation)
Reusable and efficient polyvinylpolypyrrolidone-supported triflic acid catalyst for acylation of alcohols, phenols, amines, and thiols under solvent-free conditions
Tajbakhsh, Mahgol,Tajbakhsh, Mahmoud,Khaksar, Samad,Gazvini, Helia Janatian,Heidary, Marzieh
, p. 1117 - 1122 (2017/05/10)
Abstract: A triflic acid-functionalized polyvinylpolypyrrolidone was prepared and fully characterized by FT-IR, TGA, and SEM. This super acidic solid catalyst shows high catalytic activity for selective acylation of alcohols, phenols, amines, and thiols with anhydrides under solvent-free conditions at room temperature. In addition, this method features an easy to handle solid super acid catalyst and an operationally simple procedure, affording the desired acylated products in excellent yields. Graphical abstract: [Figure not available: see fulltext.].
TETRAZOLINONE COMPOUND AND APPLICATIONS THEREOF
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Paragraph 0863, (2015/11/24)
Disclosed is a tetrazolinone compound having a high pest control effect and represented by the formula (1): wherein R1, R2, R3, and R11 each represent a halogen atom, a C1-C6 alkyl group, or the like; R4 and R5 each represent a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or the like; R6 represents a C1-C3 alkyl group which may have a halogen atom(s) or the like; R7, R8, and R9 each represent a hydrogen atom, a halogen atom, or the like; R10 represents a C1-C3 alkyl group or the like; R12 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, or the like, and R13 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, or the like.
Palladium-catalyzed annulation of 2,2′-diiodobiphenyls with alkynes: Synthesis and applications of phenanthrenes
Lin, Yu-De,Cho, Chun-Lung,Ko, Chih-Wei,Pulte, Anna,Wu, Yao-Ting
, p. 9979 - 9988 (2013/01/15)
A range of phenanthrene derivatives were efficiently synthesized by the palladium-catalyzed annulation of 2,2′-diiodobiphenyls with alkynes. The scope, limitations and regioselectivity of the reaction were investigated. The described method was adopted to synthesize 9,10-dialkylphenanthrenes, sterically overcrowded 4,5-disubstituted phenanthrenes and phenanthrene-based alkaloids. Reactions of highly methoxy-substituted biphenyls with 2-(2-propynyl)pyrrolidine and 2-(2-propynyl)piperidine gave 2-(9-phenanthylmethyl)pyrrolidines and 2-(9-phenanthylmethyl)piperidines, respectively. The products were transformed to phenanthroindolizidine and phenanthroquinolizidine alkaloids by the Pictet-Spengler reaction.
Gold(III)-catalyzed direct acetoxylation of arenes with iodobenzene diacetate
Qiu, Di,Zheng, Zhitong,Mo, Fanyang,Xiao, Qing,Tian, Yu,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 4988 - 4991 (2011/11/13)
AuCl3-catalyzed direct acetoxylation of electron-rich aromatic compounds has been achieved with iodobenzene diacetate as the acetoxylation reagent.
Iodonium Cyclophanes for SECURE Arene Functionalization
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Page/Page column 26, (2011/08/08)
This disclosure relates to compounds, reagents, and methods useful in the synthesis of aryl fluorides, for example, in the preparation of 18F labeled radiotracers. For example, this disclosure provides universal “locked” aryl substituents that result in StereoElectronic Control of Unidirectional Reductive Elimination (SECURE) from diaryliodonium salts. The reagents and methods provided herein may be used to access a broad range of compounds, including aromatic compounds, heteroaromatic compounds, amino acids, nucleotides, and synthetic compounds.
Gold-catalyzed oxidative acyloxylation of arenes
Pradal, Alexandre,Toullec, Patrick Y.,Michelet, Veronique
supporting information; scheme or table, p. 6086 - 6089 (2011/12/22)
A variety of nonactivated hindered aromatic rings are acyloxylated (22 examples, up to 83% yield) in the presence of PPh3AuCl as the catalyst and di(acetoxy)iodobenzene as the oxidant. The reaction proceeds at 110 °C in an acid media and allows the formation of both hindered acetoxy and acyloxy derivatives. This methodology nicely complements the Pd-catalyzed arene acyloxylation reaction, which is not operating on hindered substrates and allows the Au-catalyzed unprecedented acyloxylation reaction of arenes, implying various carboxylic acids.
Regiospecific reductive elimination from diaryliodonium salts
Wang, Bijia,Graskemper, Joseph W.,Qin, Linlin,DiMagno, Stephen G.
supporting information; experimental part, p. 4079 - 4083 (2010/08/07)
(Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.
Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, and thiols in room temperature Ionic liquids
Xi, Zhiwen,Hao, Wenyan,Wang, Pingping,Cai, Mingzhong
experimental part, p. 3528 - 3537 (2009/12/24)
Ruthenium(III) chloride-catalyzed acylation of a variety of alcohols, phenols, and thiols was achieved in high yields under mild conditions (room temperature) in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]). The ionic liquid and ruthenium catalyst can be recycled at least 10 times. Our system not only solves the basic problem of ruthenium catalyst reuse, but also avoids the use of volatile acetonitrile as solvent.
