33802-53-8Relevant academic research and scientific papers
A New One-pot Synthesis of Alkynylphosphonates
Lera, Manuel,Hayes, Christopher J.
, p. 3873 - 3875 (2000)
equation presented A method for the palladium-catalyzed synthesis of alkynylphosphonates from 1,1-dibromo-1-alkenes has been developed. In general, the best catalyst system for this transformation was found to be Pd(OAc)2, dppf, H-phosphonate, propylene oxide, DMF, 80°C. The reaction appears tolerant of a range of functional groups in both the 1,1-dibromo-1-alkene and H-phosphonate coupling partners. The synthesis of a backbone-modified thymidine dimer is used to illustrate the application of this methodology in the synthesis of complex target molecules.
TiO2/Cu2O nanoparticle-catalyzed direct C(sp)-P bond formation: Via aerobic oxidative coupling in air and visible light
Hosseini-Sarvari, Mona,Jafari, Fattaneh
, p. 3001 - 3006 (2020/03/13)
The synthesis of organophosphorus compounds is one of the important goals in organic chemistry. Among these compounds, alkynylphosphonates are significantly utilized as the main precursors for the synthesis of biologically active molecules in medicinal chemistry and have attracted extensive interest in the past few decades. Although few efforts have been made towards the direct and atom-economical synthesis of alkynylphosphonates, efforts towards the utilization of visible light as a green and renewable energy source have not been made to date. Here, we have promoted a strategy to construct a type of nano metal oxide composite photocatalyst (Cu2O decorated on TiO2) for the synthesis of alkynylphosphonates via direct C-P bond formation between terminal alkyne and H-phosphonate under visible light irradiation. In this p-n heterojunction photocatalyst, Cu2O acted as a visible-light absorber; moreover, the CB (conduction band) of TiO2 was favorable for accepting a photogenerated electron, and the generated electron hole (e-/h+) pair could initiate the reaction. The present study can provide a new way for the synthesis of this important class of phosphorus organic compounds.
Copper-catalyzed one-pot synthesis of alkynylphophonates
Song, Wang-Ze,Li, Jun-Hao,Li, Ming,He, Jun-Nan,Dong, Kun,Ullah, Karim,Zheng, Yu-Bin
supporting information, p. 697 - 703 (2019/02/16)
Copper is found to be an effective catalyst for the preparation of alkynylphophonates. A novel copper-catalyzed one-pot synthesis of alkynylphophonates from terminal alkynes and dialkyl phosphites is developed which involves the haloalkynes intermediates. This method provides a unique and alternative approach to the well-documented oxidative coupling or arylpropiolic acid strategies.
Aerobic oxidative alkynylation of H-phosphonates and amides: An efficient route for the synthesis of alkynylphosphonates and ynamides using a recyclable Cu-MnO catalyst
Singh, Harshvardhan,Sahoo, Tapan,Sen, Chiranjit,Galani, Sunil M.,Ghosh, Subhash Chandra
, p. 1691 - 1698 (2019/04/08)
An atom-economical and efficient route for the synthesis of alkynylphosphonates and ynamides by aerobic oxidative alkynylation of H-phosphonates and amides with both aliphatic and aromatic alkynes using our synthesized recyclable heterogeneous Cu-MnO catalyst has been developed. The phosphorylation was carried out under base- and ligand-free conditions, and in the presence of air as the sole oxidant. The reaction is compatible with a wide variety of functional groups and generates alkynylphosphonate and ynamide products in good to excellent yields. Both reactions can be scaled up to the gram scale without any decrease in the reaction yield and the reaction time is less compared to literature reports. The catalyst is recyclable and reused several times without any significant loss of reactivity.
Mukaiyama reagent-promoted metal-free preparation of alkynyl sulfones and phosphonates under mild conditions
Qi, Danyang,Dong, Wanrong,Peng, Zhihong,Zhang, Yingjun,An
, (2019/08/01)
An efficient and mild route for the formation sulfur or phosphor-substituted alkynes was herein demonstrated. The Mukaiyama reagent-mediated transformation started from easily-accessible substrates without carbon-carbon triple bonds, and the reaction proceeded under mild conditions (room temperature) in a one-pot manner, requiring for no transition metal-catalysts. The practical protocol featured for good functional groups tolerance (up to 41 examples) and high efficiency (up to 91% yields) towards alkynyl sulfones and alkynyl phosphonates at low cost.
Synthesis method of P-alkynyl phosphate compound
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Paragraph 0044; 0207-0215; 0239, (2019/04/02)
The invention relates to a synthesis method of a P-alkynyl phosphate compound. The synthesis method comprises the following steps: enabling a P-acylethyl phosphate compound, pyridinium salt and organic alkali to react with one another in an organic solven
Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) of Internal Alkynylphosphonates with High Regioselectivities under Mild Conditions
Song, Wangze,Zheng, Nan,Li, Ming,Ullah, Karim,Zheng, Yubin
supporting information, p. 2429 - 2434 (2018/05/30)
A regioselective method to access fully substituted 1,2,3-triazolyl-4-phosphonates from the internal alkynylphosphonates by rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) under mild conditions is reported. This approach is water and air compatible and has a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. Fully substituted 1,2,3-triazolyl-4-phosphonates are directly prepared from the internal alkynylphosphonates by RhAAC with high 1,4-regioselectivities. The gram-scale preparation, application to carbohydrate synthesis and the solid-phase synthesis of triazolyl-4-phosphonates are highlights of this method. (Figure presented.).
Base-Free Direct Synthesis of Alkynylphosphonates from Alkynes and H-Phosphonates Catalyzed by Cu2O
Moglie, Yanina,Mascaró, Evangelina,Gutierrez, Victoria,Alonso, Francisco,Radivoy, Gabriel
, p. 1813 - 1818 (2016/03/15)
A simple and mild methodology for the direct synthesis of alkynylphosphonates is presented. The reaction of a variety of terminal alkynes with dialkyl phosphites in the presence Cu2O (14 mol %) led to the formation of the corresponding alkynylp
Base-induced one-pot preparation of N- or P-substituted alkynes
Zhang, Yang,Zhang, Yanqin,Xiao, Jing,Peng, Zhihong,Dong, Wanrong,An, Delie
, p. 7806 - 7815 (2015/12/31)
An efficient method for the formation of C(sp)-N or C(sp)-P bonds is described. The facile transformation proceeds under mild conditions (0 or -20 °C) in a one-pot manner, and does not require transition-metal catalysts. The base-induced protocol exhibits good functional group tolerance (up to 44 examples) and high efficiency (up to 94 % yield) towards rare heteroatom-substituted acetylenes (N or P). Furthermore, the proposed mechanism was supported by the isolation of a key intermediate. An efficient method for the formation of C(sp)-N or C(sp)-P bonds is described. The facile transformation proceeds in the absence of any transition-metal catalysts under mild conditions (0 or -20 °C) in a one-pot manner with good functional group compatibility and with high efficiency.
Recognition characteristics of an adaptive vesicular assembly of amphiphilic baskets for selective detection and mitigation of toxic nerve agents
Chen, Shigui,Ruan, Yian,Brown, Jason D.,Hadad, Christopher M.,Badji, Jovica D.
, p. 17337 - 17342 (2015/02/02)
We used isothermal titration calorimetry to investigate the affinity of basket 1 (470 ?3) for trapping variously sized and shaped organophosphonates (OPs) 2-12 (137-244 ?3) in water at 298.0 K. The encapsulation is, in each case, dri
