3450-67-7Relevant articles and documents
Cycloaddition of enamines with alkynylphosphonates. A route to functionalized medium sized rings
Ruder, Suzanne M.,Norwood, Bradley K.
, p. 3473 - 3476 (1994)
Substituted seven and eight membered rings were formed from cyclopentanone and cyclohexanone via cycloadditions of pyrrolidine enamines with alkynyl phosphonates. This procedure provides straightforward access to functionalized medium sized rings that could be further manipulated in the synthesis of a number of natural products.
Hypervalent iodine in synthesis. XXVII. Alkynylphenyliodonium tosylates as alkynylating reagents: Direct conversion of alkynylphenyliodonium tosylates to dialkyl alkynylphosphonates with sodium dialkylphosphonates
Zhang, Jun-Lian,Chen, Zhen-Chu
, p. 175 - 179 (1998)
Alkynylphenyliodonium tosylates can easily react with sodium dialkylphosphonates to afford a convenient effective method for the preparation of dialkyl alkynylphosphonates.
One-pot synthesis of 1-alkynylphosphonates
Gil, Jun Mo,Sung, Jin Wuk,Park, Chan Pil,Oh, Dong Young
, p. 3171 - 3174 (1997)
1-Alkynylphosphonates 3 are prepared in a one-pot procedure from diethyl phosphorochloridates 2 and alkynyllithiums 1, which are readily generated by the reaction of 1-alkynes with n-BuLi.
Enantioselective Synthesis of Chiral Phosphonates via Rh/f-spiroPhos Catalyzed Asymmetric Hydrogenation of β,β-Disubstituted Unsaturated Phosphonates
Wang, Chaoqiong,Xie, Fang,Guo, Qianling,Xie, Chaochao,Zi, Guofu,Ye, Weiping,Zhou, Zhangtao,Hou, Guohua,Zhang, Zhanbin
, p. 12034 - 12045 (2021/08/24)
The first asymmetric hydrogenation of β,β-diaryl unsaturated phosphonates has been realized for synthesis of β,β-diaryl chiral phosphonates with excellent enantioselectivities (up to 99.9% ee) catalyzed by the Rh-(R,R)-f-spiroPhos complex. Furthermore, this catalyst also exhibits comparably excellent performance for β-aryl-β-alkyl unsaturated phosphonates providing the corresponding chiral phosphonates with up to 99.9% ee values. This methodology provides a straightforward access to asymmetric synthesis of chiral phosphonates.
Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and t-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones
Maciás-Benítez, Pablo,Sierra-Padilla, Alfonso,Tenorio, Manuel J.,Moreno-Dorado, F. Javier,Guerra, Francisco M.
, p. 16409 - 16424 (2021/11/16)
Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)4]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding β-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.
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.
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.
C-P bond construction catalyzed by NiII immobilized on aminated Fe3O4@TiO2 yolk-shell NPs functionalized by (3-glycidyloxypropyl)trimethoxysilane (Fe3O4@TiO2 YS-GLYMO-UNNiII
Ghasemzadeh, Maryam Sadat,Akhlaghinia, Batool
, p. 5341 - 5356 (2019/04/05)
NiII immobilized on aminated Fe3O4@TiO2 yolk-shell NPs functionalized by (3-glycidyloxypropyl)trimethoxysilane (Fe3O4@TiO2 YS-GLYMO-UNNiII) was prepared as a stable, h
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.
Synthesis of 1,2,3-triazolyl-5-diethylphosphonate by domino reaction
Tripolszky, Anna,Tóth, Emese,Bálint, Erika
, p. 377 - 378 (2019/01/04)
The synthesis of 1,2,3-triazolyl-5-diethylphosphonate was studied by the domino reaction of benzyl azide, phenylacetylene and diethyl phosphite. The effect of the reaction stoichiometry, the atmosphere and the amount of the catalyst were investigated.
