16244-50-1Relevant academic research and scientific papers
TfOH-Catalyzed Phosphinylation of 2,3-Allenols into ?-Ketophosphine Oxides
Zhao, Runmin,Huang, Xianhua,Wang, Minning,Hu, Shanshan,Gao, Yuxing,Xu, Pengxiang,Zhao, Yufen
, p. 8185 - 8195 (2020/09/21)
The first facile and efficient acid-catalyzed direct coupling of a wide range of unprotected 2,3-allenols with arylphosphine oxides was developed, offering a general, one-step approach for the synthesis of structurally diverse ?-ketophosphine oxides accompanied by concurrent C-P/Ca?O bond formation with remarkable functional group tolerance and complete atom-economy under metal- A nd additive-free conditions. Mechanistic studies showed that this transformation involved a rearrangement and a phospha-Michael reaction.
Potassium carbonate promoted nucleophilic addition of alkenes with phosphites
Huang, Zhenjun,Liu, Wei,Li, Sen,Yang, Yutian,Guo, Shengmei,Cai, Hu
supporting information, p. 1295 - 1297 (2020/08/21)
A facile hydrophosphonylation of alkenes by phosphites promoted by potassium carbonate was developed. The reaction features include easy handling, environmental friendliness, and avoidance of the use of strong bases. A variety of alkenes are tolerated in this reaction, with moderate to excellent yields.
Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
Moglie, Yanina,González-Soria, María José,Martín-García, Iris,Radivoy, Gabriel,Alonso, Francisco
supporting information, p. 4896 - 4907 (2016/10/06)
The hydrophosphination of carbon-carbon multiple bonds has been generally performed under acid, base or metal catalysis in different solvents. Herein, alkyl and alkenyl tertiary phosphines are obtained by the addition of diphenylphosphine to alkenes and alkynes, respectively, in the absence of a solvent and a catalyst. In the presence of elemental sulfur, the corresponding alkyl and alkenyl tertiary phosphine sulfides are synthesized in a three-component process. These simple methods, which meet most of the principles of Green Chemistry, are highly regioselective towards the anti-Markovnikov products and diastereoselective towards the Z alkenyl phosphines. The mechanistic aspects of the reactions are also tackled and the efficiency of the latter is compared with that of the catalytic methods.
Synthesis of new phosphonoamide and phosphonocaprolactam derivatives via the diethyl chlorophosphate-promoted beckmann rearrangement of γ-phosphonyloximes
Wahbi, Aymen,Touil, Soufiane
, p. 397 - 404 (2017/02/14)
ABSTRACT: Herein, we report an efficient and straightforward synthesis of new phosphonoamide and phosphonocaprolactam derivatives, via the Beckmann rearrangement of γ-phosphonyloximes. The reaction proceeded smoothly in the presence of diethyl chlorophosp
β-Diphenylphosphorylated alkanones and related compounds: Synthesis and structure
Goryunov,Bodrin,Goryunova,Nelyubina,Petrovskii,Strelkova,Peregudov,Matveeva,Pasechnik,Matveev,Nifant'Ev
, p. 780 - 791 (2014/01/23)
The reactions of diphenyl(diisopropyl)chlorophosphine with arylidene(heteroarylidene)-acetones and 3-benzylidenepentane-2,4-dione in the presence of acetic acid proceed at a high rate at room temperature to afford the corresponding β-diorganylphosphorylated alkanones and alkanediones in high yields. The reaction of diphenylchlorophosphine with 4-methoxybut-3-en-2-one and dibenzylideneacetone carried out under similar conditions at the equimolar reagent ratio can serve as a convenient method for the synthesis of unique β-diphenylphosphorylalkenones. The structures of compounds obtained were established by IR, Raman, and NMR spectroscopy and X-ray diffraction.
Dual Radical/Polar Pudovik Reaction: Application Field of New Activation Methods
Semenzin, Delphine,Etemad-Moghadam, Guita,Albouy, Dominique,Diallo, Ousmane,Koenig, Max
, p. 2414 - 2422 (2007/10/03)
The Pudovik reaction (addition of organophosphorus compounds containing a labile P-H bond with alkenes and alkynes) can progess via a radical or (and) ionic mechanism. A comparative and systematic study including various reagents and different activation methods (heating, photochemical or ultrasonic irradiation, and dry medium supported reactions) is presented. Photolysis is the most efficient method for the radical processes, but in a few examples, ultrasonic irradiation can be more appropriate since the reaction time is shorter and ultrasound did not induce side-reactions (in particular Z/E isomerization). Dry medium process on basic solid support is the best anionic activation (yield, time, selectivity, purification facilities). Ultrasound, by its mechanical effects, can contribute to increase yield compared to the classical thermal method under these basic conditions. All the activation methods are efficient whatever the unsaturated substrates for the phosphine reactivity, whereas the appropriate activation method is exclusively determined by the nature of the unsaturated system for the thiophosphine (or phosphine oxide) reactivity.
