115-89-9Relevant academic research and scientific papers
Efficient and convenient one-pot synthesis of phosphoramidates and phosphates
Gupta,Acharya,Dubey,Kaushik
, p. 3403 - 3407 (2007)
A simple and efficient one-pot method is described for the synthesis of phosphoramidates/phosphates in excellent yields from dialkylphosphites and trichloroisocyanuric acid in acetonitrile and subsequent treatment with dialkyl amines/alcohols. The procedure is operationally simple, has reduced reaction times, and uses a one-pot procedure. Copyright Taylor & Francis Group, LLC.
Zinc-catalyzed transformation of diarylphosphoryl azides to diarylphosphate esters and amides
Ying, Jun,Gao, Qian,Wu, Xiao-Feng
, p. 1540 - 1543 (2020/04/15)
We have developed a facile and efficient procedure for the synthesis of diarylphosphate esters and amides. Using Zn(acac)2 as the catalyst, the reaction of diarylphosphoryl azides with aliphatic alcohols and phenols through an unusual P?N bond cleavage provided a number of diarylphosphate esters in good yields (22 examples, up to 94%). Additionally, various diarylphosphate amides were obtained from the corresponding amines in excellent yields as well (8 examples, up to 96%).
Recyclable copper catalyst on chitosan for facile preparation of alkyl/aryl mixed phosphates via deaminated esterification between diphenylphosphoryl azides and aliphatic alcohols
Hao, Qingqing,Hong, Qian,Jiao, Lin-Yu,Li, Zhuo,Liu, Shanshan,Ma, Xiao-Xun,Ning, Zi-Hui,Sun, Ming,Xu, Long,Zhang, Ze
, (2020/07/15)
An efficient methodology was established for the preparation of alkyl/aryl mixed phosphates under aerobic conditions promoted by a easily recoverable heterogeneous catalyst. This highly active copper catalyst was obtained by directly mixing of copper precursor with chitosan solution, followed by a simple work-up process. In this catalytic system, different phosphoryl azides and aliphatic alcohols were employed to generate desired products in moderate to excellent yields with good functional group tolerance. This protocol provided a practical application of the chitosan supported heterogeneous copper catalyst towards a novel P–O bond formation.
Method for catalytically synthesizing phosphoric acid mixed ester compound by using chitosan-loaded copper
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Paragraph 0061-0065, (2020/10/19)
The invention relates to a method for synthesizing a phosphoric acid mixed ester compound under the catalysis of chitosan-loaded copper. The preparation method comprises the following steps of: sequentially adding an azido phosphate compound, a chitosan-l
Copper catalyzed synthesis of aryl/alkyl mixed phosphates from diphenylphosphoryl azides and aliphatic alcohols under mild conditions
Jiao, Lin-Yu,Zhang, Ze,Yin, Xiao-Mei,Li, Zhuo,Ma, Xiao-Xun
, p. 39 - 45 (2019/10/03)
An efficient and convenient one-pot protocol is developed to prepare aryl/alkyl mixed phosphates in the presence of copper catalyst under exceptionally mild conditions. A series of versatile, ubiquitous, and inexpensive phosphoryl azides and aliphatic alcohols are combined for the first time ever. Diphenylphosphoryl azide is employed as novel phosphors reagent through an unexpected cleavage of P[sbnd]N bond. The transformation is advantageous with respect to a broad of functional group compatibility and different esterification products are isolated in good to excellent results. This new catalytic system represents a superior platform towards a mild, operationally simple, practical, and scalability alternative to access target molecules. Furthermore, a plausible mechanism is proposed based on insightful mechanistic studies.
Synthesis method of copper-catalyzed phosphate mixed ester compound
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Paragraph 0036-0038, (2019/10/17)
The invention provides a synthesis method of a copper-catalyzed phosphate mixed ester compound. The synthesis method comprises the steps that a phosphate ester azide compound and fatty alcohol are mixed, then a copper catalyst is added, alkali is added, reaction is conducted at the temperature of 20-100 DEG C for 3-24 h, and the phosphate mixed ester compound is obtained through aftertreatment. According to the synthesis method, the phosphate ester azide compound and the fatty alcohol are adopted to synthesize the phosphate mixed ester compound for the first time, in the synthesis process, only the copper catalyst and the alkali with the catalytic dosage are needed to be added, operation is easy, the defect of needing inert gas protection is overcome, and the synthesis method is novel andefficient.
DCC-assisted direct esterification of phosphinic and phosphoric acids with O-nucleophiles
Xiong, Biquan,Wang, Gang,Zhou, Congshan,Liu, Yu,Li, Jiandong,Zhang, Pangliang,Tang, Kewen
supporting information, p. 239 - 244 (2017/11/20)
A novel and efficient dicyclohexylcarbodiimide-promoted protocol for the selective and controllable esterification of P(O)OH compounds using O-nucleophiles (alcohols and phenols) as efficient esterification reagents is described. This method features a high efficiency and good functional-group tolerance, meaning a simple way to synthesize a broad spectrum of phosphinic and phosphoric acid esters from basic starting materials with moderate to excellent yields.
Direct aerobic oxidative esterification and arylation of P(O)-OH compounds with alcohols and diaryliodonium triflates
Xiong, Biquan,Feng, Xiaofeng,Zhu, Longzhi,Chen, Tieqiao,Zhou, Yongbo,Au, Chak-Tong,Yin, Shuang-Feng
, p. 537 - 543 (2015/04/14)
Copper-catalyzed aerobic oxidative esterification of P(O)-OH compounds is achieved using alcohols as efficient esterification reagents, giving the expected products with good to moderate yields. Furthermore, it is shown that the arylation of P(O)-OH compounds proceeds efficiently to produce the corresponding products via the treatment of diaryliodonium triflates under mild reaction conditions. It is a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. The protocol is convenient for practical application. A plausible mechanism has been proposed for the reaction.
Simple and compelling biomimetic metal-organic framework catalyst for the degradation of nerve agent simulants
Katz, Michael J.,Mondloch, Joseph E.,Totten, Ryan K.,Park, Jin K.,Nguyen, Sonbinh T.,Farha, Omar K.,Hupp, Joseph T.
, p. 497 - 501 (2014/01/23)
Inspired by biology, in which a bimetallic hydroxide-bridged zinc(II)-containing enzyme is utilized to catalytically hydrolyze phosphate ester bonds, the utility of a zirconium(IV)-cluster-containing metal-organic framework as a catalyst for the methanolysis and hydrolysis of phosphate-based nerve agent simulants was examined. The combination of the strong Lewis-acidic ZrIV and bridging hydroxide anions led to ultrafast half-lives for these solvolysis reactions. This is especially remarkable considering that the actual catalyst loading was a mere 0.045 % as a result of the surface-only catalysis observed. Nervous breakdown: UiO-66, a biomimetic metal-organic framework based on a zirconium oxo cluster, is capable of rapidly catalyzing the breakdown of phosphate-based nerve agent simulants. UiO-66 catalyzes both methanolysis and hydrolysis of the nerve agent simulant methyl paraoxon (shown in the graphic, R=CH3) with high catalytic efficiency.
Enhanced catalytic decomposition of a phosphate triester by modularly accessible bimetallic porphyrin dyads and dimers
Totten, Ryan K.,Ryan, Patrick,Kang, Byungman,Lee, Suk Joong,Broadbelt, Linda J.,Snurr, Randall Q.,Hupp, Joseph T.,Nguyen, Sonbinh T.
supporting information; experimental part, p. 4178 - 4180 (2012/05/05)
A series of metalloporphyrin dimers were modularly prepared and shown to catalyze the methanolysis of a phosphate triester, yielding rates that are large compared to the rate of the uncatalyzed reaction. Up to 1300-fold rate acceleration can be achieved v
