1754-49-0Relevant academic research and scientific papers
CuSO4/Al2O3 as a new effective and recyclable catalyst for the arylation of dialkyl phosphites
Karlstedt,Anokhin,Beletskaya
, p. 2498 - 2499 (2013)
A new effective recycled catalyst CuSO4/Al2O 3, which performs the phosphorylation of aryl halides and bromostyrene, was proposed.
Product selectivities and third-order rate laws for solvolyses of ethyl phenylphosphonochloridate in aqueous alcohols
Bentley, T. William,Ebdon, David N.
, p. 759 - 763 (2001)
Rate constants and product selectivities (S) for solvolyses of ethyl phenylphosphonochloridate [PhP(=O)OEtCl] in aqueous ethanol and methanol at 0°C are reported; S = ([ester product]/[acid product]) x ([water]/[alcohol solvent]). The results show trends
An intramolecular Arbuzov rearrangement initiated by anodic oxidation
Yasui, Shinro,Shioji, Kosei,Tsujimoto, Munekazu,Ohno, Atsuyoshi
, p. 1625 - 1628 (1996)
Dialkyl phenylphosphonite PhP(OR)2 (R = Et, Me) undergoes an intramolecular Arbuzov rearrangement upon electrolysis at an anode in acetonitrile under an oxygen atmosphere to yield alkyl alkylphenylphosphinate PhRP(=O)(OR). The results here suggest that the rearrangement takes place through a radical-chain mechanism initiated by anodic oxidation of the phosphonite to the corresponding cation radical.
Heterogeneous Organophosphate Ethanolysis: Degradation of Phosphonothioate Neurotoxin by a Supported Molybdenum Peroxo Polymer
Kuo, Louis Y.,Bennett, Andrew,Miao, Qianli
, p. 10013 - 10020 (2017)
A polystyrene-supported molybdenum peroxo material [Mo-Y(s)] was applied toward the oxidative degradation of the organophosphate neurotoxin O,S-diethylphenyl phosphonothioate (1) through ethanolysis. In addition to the operational advantages of the heterogeneous reactivity, oxidative ethanolysis with a 10-fold excess of hydrogen peroxide yields only P-S bond scission to produce diethylphenyl phosphonate and ethyl sulfate. This is the first report of a molybdenum solid support that promotes the degradation of sulfur-containing organophosphate with the turnover benefits of heterogeneous catalysis. The activation parameters of 1 ethanolysis by Mo-Y(s) (Ea = 57 ± 6 kJ/mol and ΔS? = -124 ± 21 J/mol·K) and by the model compound oxodiperoxo(pyridine-2-carboxylato)molybdate(VI) bis(pyridine-2-carboxylic acid) monohydrate (3; Ea = 55 ± 5 kJ/mol and ΔS? = -154 ± 15 J/mol·K) are almost identical for the oxidation of thioanisole by 3. This suggests that the rate-determining step for 1 ethanolysis is sulfur oxidation to form an intermediate phosphonothioate S-oxide, which subsequently undergoes nucleophilic attack by the ethanol solvent to form diethylphenyl phosphonate and ethyl sulfate. Evidence for the formation of this S-oxide intermediate and the postulated ethanolysis mechanism is provided.
Evaluation of transition metal catalysts in electrochemically induced aromatic phosphonation
Strekalova, Sofia,Khrizanforov, Mikhail,Budnikova, Yulia
, (2019)
Voltammetry provides important information on the redox properties of catalysts (transition metal complexes of Ni, Co, Mn, etc.) and their activity in electrocatalytic reactions of aromatic C-H phosphonation in the presence of a phosphorus precursor, for
New method of metal-induced oxidative phosphorylation of benzene
Khrizanforov,Strekalova,Gryaznova,Khrizanforova,Budnikova, Yu. H.
, p. 1926 - 1932 (2015)
A new approach to phosphorylation of benzene with diethyl phosphite is suggested, which is based on the electrocatalytic oxidation of a mixture of benzene and diethyl phosphite (1 : 1) under mild conditions (room temperature, normal pressure) in the presence of bimetallic catalytic systems MnII/CoIIL (MnSO4/CoCl2dmphen or MnCl2/CoCl2bipy). This method gives diethyl phenylphosphonate in high yield (up to 90%) and practically 100% conversion of the phosphite.
Direct Near Infrared Light–Activatable Phthalocyanine Catalysts
Katsurayama, Yoshino,Ikabata, Yasuhiro,Maeda, Hajime,Segi, Masahito,Nakai, Hiromi,Furuyama, Taniyuki
supporting information, (2021/12/22)
The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activa
Controlling Chemoselectivity of Catalytic Hydroboration with Light
Bergamaschi, Enrico,Chen, Yi-Kai,Hohenadel, Melissa,Lunic, Danijela,McLean, Liam A.,Teskey, Christopher J.
supporting information, (2022/01/13)
The ability to selectively react one functional group in the presence of another underpins efficient reaction sequences. Despite many designer catalytic systems being reported for hydroboration reactions, which allow introduction of a functional handle fo
Radical Chain Reduction via Carbon Dioxide Radical Anion (CO2?-)
Hendy, Cecilia M.,Smith, Gavin C.,Xu, Zihao,Lian, Tianquan,Jui, Nathan T.
, p. 8987 - 8992 (2021/07/01)
We developed an effective method for reductive radical formation that utilizes the radical anion of carbon dioxide (CO2?-) as a powerful single electron reductant. Through a polarity matched hydrogen atom transfer (HAT) between an electrophilic radical and a formate salt, CO2?- formation occurs as a key element in a new radical chain reaction. Here, radical chain initiation can be performed through photochemical or thermal means, and we illustrate the ability of this approach to accomplish reductive activation of a range of substrate classes. Specifically, we employed this strategy in the intermolecular hydroarylation of unactivated alkenes with (hetero)aryl chlorides/bromides, radical deamination of arylammonium salts, aliphatic ketyl radical formation, and sulfonamide cleavage. We show that the reactivity of CO2?- with electron-poor olefins results in either single electron reduction or alkene hydrocarboxylation, where substrate reduction potentials can be utilized to predict reaction outcome.
Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions
Farrokhi, Alireza,Rouzifar, Majid,Sansano, José Miguel,Sobhani, Sara
, p. 19963 - 19976 (2021/11/12)
A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.
