41532-81-4Relevant academic research and scientific papers
Electrophotocatalytic C?H Heterofunctionalization of Arenes
Huang, He,Lambert, Tristan H.
supporting information, p. 11163 - 11167 (2021/04/19)
The electrophotocatalytic heterofunctionalization of arenes is described. Using 2,3-dichloro-5,6-dicyanoquinone (DDQ) under a mild electrochemical potential with visible-light irradiation, arenes undergo oxidant-free hydroxylation, alkoxylation, and amination with high chemoselectivity. In addition to batch reactions, an electrophotocatalytic recirculating flow process is demonstrated, enabling the conversion of benzene to phenol on a gram scale.
Palladium-Catalyzed C(sp3)?H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group
St John-Campbell, Sahra,Ou, Alex K.,Bull, James A.
supporting information, p. 17838 - 17843 (2018/11/23)
C?H Functionalization of amines is a prominent challenge due to the strong complexation of amines to transition metal catalysts, and therefore typically requires derivatization at nitrogen with a directing group. Transient directing groups (TDGs) permit C?H functionalization in a single operation, without needing these additional steps for directing group installation and removal. Here we report a palladium catalyzed γ-C?H arylation of amines using catalytic amounts of alkyl acetals as transient activators (e.g. commercially available (2,2-dimethoxyethoxy)benzene). This simple additive enables arylation of amines with a wide range of aryl iodides. Key structural features of the novel TDG are examined, demonstrating an important role for the masked carbonyl and ether functionalities. Detailed kinetic (RPKA) and mechanistic investigations determine the order in all reagents, and identify cyclopalladation as the turnover limiting step. Finally, the discovery of an unprecedented off-cycle free-amine directed ?-cyclopalladation of the arylation product is reported.
Benzene C-H Etherification via Photocatalytic Hydrogen-Evolution Cross-Coupling Reaction
Zheng, Yi-Wen,Ye, Pan,Chen, Bin,Meng, Qing-Yuan,Feng, Ke,Wang, Wenguang,Wu, Li-Zhu,Tung, Chen-Ho
supporting information, p. 2206 - 2209 (2017/05/12)
Aryl ethers can be constructed from the direct coupling between the benzene C-H bond and the alcohol O-H bond with the evolution of hydrogen via the synergistic merger of photocatalysis and cobalt catalysis. Utilizing the dual catalyst system consisting of 3-cyano-1-methylquinolinum photocatalyst and cobaloxime, intermolecular etherification of arenes with various alcohols and intramolecular alkoxylation of 3-phenylpropanols with formation of chromanes are accomplished. These reactions proceed at remarkably mild conditions, and the sole byproduct is equivalent hydrogen gas.
High-Throughput Screening Protocol for the Coupling Reactions of Aryl Halides Using a Colorimetric Chemosensor for Halide Ions
Eom, Min Sik,Noh, Jieun,Kim, Han-Sung,Yoo, Soyeon,Han, Min Su,Lee, Sunwoo
supporting information, p. 1720 - 1723 (2016/05/19)
Mercury complex of 4-(2-pyridylazo)resorcinol (PAR-2Hg2+), a halide-ion chemosensor, was prepared and its efficiency as a tool for high-throughput screening (HTS) of transition-metal-catalyzed coupling reactions was investigated. It showed a high selectivity for halide ions. When the PAR-2Hg2+ complex was used in the Suzuki coupling reaction and C-H activated coupling reaction with aryl bromides, the quantitative and qualitative conversions of aryl halides were obtained from the reaction mixture color change.
Behaviour of iprit carbonate analogues in solventless reactions
Arico',Evaristo,Tundo
, p. 31071 - 31078 (2014/08/05)
Sulfur iprit carbonate analogues have been investigated in neat conditions at atmospheric pressure, in the presence and in the absence of a catalytic amount of base. Furthermore, their reaction mechanism has been discussed in detail. In these novel reaction conditions, sulfur mustard carbonate analogues, that previously showed poor or no reactivity, remarkably undergo efficient nucleophilic substitution with several substrates. This journal is the Partner Organisations 2014.
Sulfur and nitrogen mustard carbonate analogues
Arico, Fabio,Chiurato, Matteo,Peltier, Josephine,Tundo, Pietro
scheme or table, p. 3223 - 3228 (2012/07/31)
Sulfur and nitrogen half-mustard compounds lose their aggressive properties when the chlorine atom is replaced by a carbonate moiety. The anchimeric effect of the novel mustard carbonate analogues is investigated. The reaction follows first-order kinetics, does not need any base, and occurs with -OH, -NH and acidic -CH nucleophiles. Most of these molecules are unexplored and might provide a novel strategy for the preparation of compounds previously not easily accessible. Copyright
2-Phenoxyethanol derived diselenide and related compounds; Synthesis of a seven-membered seleninate ester
Tripathi, Santosh K.,Sharma, Sagar,Singh, Harkesh B.,Butcher, Ray J.
scheme or table, p. 581 - 587 (2011/03/17)
Syntheses of several diorganodiselenides and, in particular, a seven-membered cyclic seleninate ester derived from 2-phenoxyethanol are described. The seleninate ester was obtained from allyl (2-(2-hydroxyethoxy) phenyl) selenide through a series of oxidation and [2,3] sigmatropic rearrangement steps. The ester exhibits good GPx-like activity in the coupled reductase assay.
Diazotisation of aromatic amines and solvolysis of diazonium salts in ethylene glycol ethers
Ram, Ram N.,Singh, Virinder
, p. 800 - 803 (2007/10/03)
Aniline and unhindered alkyl-substituted anilines undergo solvolysis in dioxane and DME saturated with dry hydrogen chloride on diazotisation with isoamyl nitrite to give 2-(2-chloroethoxy)ethyl aryl ethers and 2-methoxyethyl aryl ethers respectively in 36-47% yields. 2,6-Dialkyl-substituted anilines give the corresponding chloro compounds as the major product along with the aryl ethers in lower yields. Diazotisation of aniline in ethylene glycol and monomethyl ethers of ethylene glycol and diethylene glycol gave the corresponding alcoholysis products in low yields. The solvolysis of aniline did not occur on diazotisation in diethyl ether or THF.
Keratinocyte growth inhibitors and hydroxamic acid derivatives
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Page 23, (2010/02/06)
This invention relates to a keratinocyte-proliferation inhibitor comprising as active ingredient a compound having an activity of inhibiting the solubilization of heparin-binding EGF-like growth factor bound to cell membranes and a compound of the formula (I); or pharmaceutically acceptable salt thereof, wherein R1, R2, R3 are hydrogen atom or alkyl and X is substituted benzene or the like.
Process for the preparation of 2-methoxyethoxy-benzenes and novel 2-methoxyethoxy-benzyl cyanides
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, (2008/06/13)
2-Methoxyethoxy-benzenes are obtained in an advantageous manner from the corresponding phenol compounds by reaction with 2-chloroethyl methyl ether if the process is carried out without the addition of a strong solvent at temperatures above 95° C. and under pressure. The present invention also relates to novel 2-methoxyethoxy-benzyl cyanides.
