80359-63-3Relevant academic research and scientific papers
Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds
Xu, Kaiqiang,Liu, Long,Li, Zhaohui,Huang, Tianzeng,Xiang, Kang,Chen, Tieqiao
, p. 14653 - 14663 (2020/12/29)
The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.
Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds
Kurosawa, Miki B.,Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
supporting information, p. 7386 - 7392 (2020/04/30)
We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate.
Preparation method of arylalkyl phosphorus oxide compounds
-
Paragraph 0054; 0055, (2019/04/09)
A preparation method of arylalkyl phosphorus oxide compounds is provided. The invention discloses a preparation method of several arylalkyl phosphorus oxide compounds. The preparation method includes:taking diphenylphosphine oxyhydrogen of 1.3 equivalent, 2.5% by mass nickel catalyst (with or without ligands) or palladium catalyst with ligands and a base of 1.5 equivalent from a glovebox, addingthem sequentially into a Schlenk reaction tube, adding a nitrile compound of 1.0 equivalent, vacuumizing, and backfilling with nitrogen; in the nitrogen atmosphere, adding a solvent, and allowing reaction to occur continuously at 120 DEG C for 16 h; after reaction, cooling to room temperature, and performing column chromatography separation to obtain the target product under high selectivity and high yield. The preparation method herein allows sp3C-CN\P-H cross coupling; reaction conditions are mild; operating is easy; the preparation process is simple; the target product has high conversion rate and high yield; the problems of other synthetic methods are solved that, for instance, two-step reaction system is complex, many organic and inorganic byproducts are produced, environmental pollution is caused easily, and the substrate range is narrow; the preparation method has a good industrial application prospect.
Catalytic sp3C-CN Bond Cleavage: Ni-Mediated Phosphorylation of Alkylnitriles
Zhang, Ji-Shu,Chen, Tieqiao,Zhou, Yongbo,Yin, Shuang-Feng,Han, Li-Biao
supporting information, p. 6746 - 6749 (2018/10/25)
A direct phosphorylation of the sp3C-CN bond catalyzed by a nickel catalyst is disclosed. A wide range of primary nitriles readily coupled with secondary phosphine oxides to produce the corresponding phosphorylated products in high yields. As a key step, this new method was applied to the synthesis of anticancer drug Combretastatin-A4, significantly shortening its synthetic path.
Carbon Acidity. 63. Equilibrium Ion Pair Acidities of Some Phosphorus-Substituted Carbon Acids
Streitwieser, Andrew,Juaristi, Eusebio
, p. 768 - 770 (2007/10/02)
Ion-pair C-H acidities are reported as pKCsCHA for bis(diphenylphosphino)methane (1, 31.1), (p-phenylbenzyl)diphenylphosphine (3, 31.0), p-tolyldiphenylphosphine (4, 37.9), and several of the corresponding phosphine oxides.The diphenylphosphine group is about as anion stabilizing as p-biphenyl.The Ph2P(O) group is additionally stabilizing because of enhanced ion-pair interaction.The pKCsCHA of benzyldiphenylphosphine (2) can be estimated to be about 32.
