1706-96-3Relevant academic research and scientific papers
Photoinduced oxidation of triphenylphosphine isolated in a low-temperature oxygen matrix
Reva, Igor,Lapinski, Leszek,Nowak, Maciej J.
, p. 97 - 100 (2008)
Photooxidation reactions of triphenylphosphine (Ph3P) monomers isolated in matrices of solid oxygen at 10 K were characterized by means of infrared spectroscopy. Upon UV (λ > 280 nm) irradiation of O2 matrices, ca. 90% of Ph3P was converted to triphenylphosphine oxide (Ph3P{double bond, long}O), with concomitant formation of ozone. In the competing photoreaction, ca. 10% of Ph3P was converted to diphenyl-phenyl-phosphinate, Ph2(Ph-O-)P{double bond, long}O. The interpretation was assisted by theoretical [DFT(B3LYP)/6-31G(d, p)] calculations of vibrational spectra, as well as by comparison with the experimental vibrational data from separate experiments in which monomeric Ph3P and Ph3P{double bond, long}O were isolated in argon and oxygen matrices at 10 K.
A Novel Phosphorus -> Oxygen Phenyl Migration: Triphenylphosphine Dioxide as a Reaction Intermediate
Itzstein, Mark von,Jenkins, Ian D.
, p. 164 - 165 (1983)
Treatment of triphenylphosphine with diethyl azodicarboxylate and hydrogen peroxide results in the formation of phenyl diphenylphosphinate; triphenylphosphine dioxide is suggested as an intermediate.
Electrochemical Enabled Cascade Phosphorylation of N?H/O?H/S?H Bonds with P?H Compounds: An Efficient Access to P(O)-X Bonds
Abdukader, Ablimit,Dong, Xiaojuan,Jin, Weiwei,Liu, Chenjiang,Wang, Bin,Wang, Ruige,Xia, Yu,Xue, Fei,Zhang, Yonghong
supporting information, p. 14931 - 14935 (2021/10/06)
An electrochemical three component cascade phosphorylation reaction of various heteroatoms-containing nucleophiles including carbazoles, indoles, phenols, alcohols, and thiols with Ph2PH has been established. Electricity is used as the “traceless” oxidant and water and air are utilized as the “green” oxygen source. All kinds of structurally diverse organophosphorus compounds with P(O)-N/P(O)-O/P(O)-S bonds are assembled in moderate to excellent yields (three categories of phosphorylation products, 50 examples, up to 97 % yield). A tentative free radical course is put forward to rationalize the reaction procedure.
Tf2O/DMSO-Promoted P-O and P-S Bond Formation: A Scalable Synthesis of Multifarious Organophosphinates and Thiophosphates
Shen, Jian,Li, Qi-Wei,Zhang, Xin-Yue,Wang, Xue,Li, Gui-Zhi,Li, Wen-Zuo,Yang, Shang-Dong,Yang, Bin
supporting information, p. 1541 - 1547 (2021/04/05)
A Tf2O/DMSO-based system for the dehydrogenative coupling of a wide range of alcohols, phenols, thiols, and thiophenols with diverse phosphorus reagents has been developed. This metal- and strong-oxidant-free strategy provides a facile approach to a great variety of organophosphinates and thiophosphates. The simple reaction system, good functional-group tolerance, and broad substrate scope enable the application of this method to the modification of natural products and the direct synthesis of bioactive molecules and flame retardants.
Palladium-catalyzed solvent-free preparation of arylphosphonates Arp(O)(OAr)2 from (Aro)3p via the Michaelis-Arbuzov rearrangement
Li, Chunya,Han, Li-Biao
supporting information, p. 3613 - 3617 (2020/11/03)
The Pd-catalyzed Michaelis-Arbuzov rearrangement of triaryl phosphites to produce the corresponding arylphosphonates in good to excellent yields is disclosed. In comparison to the traditional methods, this new method is highly atom efficient and is general, as it can be readily extended to aryl phosphonites and phosphinites. A gram-scale reaction of (PhO)3P to PhP(O)(OPh)2 with low loading of the catalyst was also demonstrated to show its potentially practical usefulness. A plausible mechanism is proposed.
Base-promoted selective O-phosphorylation of aryl triflates with P(O)-H compounds
Wang, Mingyue,Yang, Jia,Wang, Shuai,Zhong, Hong
supporting information, (2020/05/05)
Compared to previous transition metal-catalyzed C-phosphorylation reactions for constructing C–P bonds, in the absence of transition metal catalysts and ligands, a direct O-phosphorylation of aryl triflates selectively occurred with P(O)-H compounds in the presence of a base via the construction of O–P bonds. This transformation proceeds under simple and mild conditions, and provides a new method for the preparation of valuable organophosphoryl compounds from readily available P(O)-H compounds and triflates.
Phosphonate compound, preparation method and application thereof
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Paragraph 0053-0055, (2020/04/02)
The invention provides a phosphonate compound, a preparation method and application thereof. The method includes the steps of: in a nitrogen atmosphere, mixing a P(O)-H compound, an aryl trifluoromethanesulfonate compound, an alkali reagent and an organic solvent, carrying out stirring reaction at 80-130DEG C for 15-24h, and conducting cooling, washing and extraction at the end of reaction to obtain an organic phase; drying and distilling the obtained organic phase to obtain the phosphonate compound; wherein the molar ratio of the P(O)-H compound, the aryl trifluoromethanesulfonate compound and the alkali reagent is 1-3:1:2-3. The method has the advantages of simple and easily available raw materials, simple reaction conditions, wide functional group compatibility, high yield and wide applicability, the structural formula of the obtained phosphonate compound is shown as formula (I) in the specification, and the extraction rate of the phosphonate compound applied to the field of lithiumion extraction is 53% or above.
A phosphoryl radical-initiated Atherton-Todd-type reaction under open air
Ou, Yingcong,Huang, Yuanting,He, Zhenlin,Yu, Guodian,Huo, Yanping,Li, Xianwei,Gao, Yang,Chen, Qian
supporting information, p. 1357 - 1360 (2020/02/11)
A phosphoryl radical-initiated Atherton-Todd-type reaction using air as the radical initiator and CHCl3 as the halogenating reagent for the phosphorylation of alcohols, phenols, and amines has been developed. This novel transformation provides a highly efficient route to important phosphinates, phosphinic amides, and phosphoramidates in up to 99% yield with a broad substrate scope under very mild conditions (48 examples).
Highly Efficient and Convenient Access to Phosphinates via CHCl3-Assisted Direct Phosphorylation between R2P(O)H and ROH by Phosphonium Salt Catalysis
Jiang, Zhiyu,Wang, Tianli,Yu, Xiaojun,Zhang, Hong-Su,Zhang, Song
supporting information, (2020/05/25)
A mild, efficient, convenient and scalable method to synthesize phosphinates via direct phosphorylation between R2P(O)H and ROH was developed. All aromatic substrates completed this transformation with excellent yields (up to 98 %), and preliminary mechanistic studies suggest that a carbene-involving process from CHCl3 to CH2Cl2 facilitates the phosphorylation.
Preparation method of compound containing P-O bond or P-S bond
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Paragraph 0287-0291, (2020/09/12)
The invention discloses a preparation method of a compound containing a P-O bond or a P-S bond. The method comprises the following steps: a compound containing hydroxyl or sulfydryl and a phosphorus reagent are taken as initial raw materials; then, the initial raw materials are put into an inert gas atmosphere; and under the action of trifluoromethanesulfonic anhydride (Tf2O) and dimethyl sulfoxide (DMSO), the compound containing hydroxyl or sulfydryl, the phosphorus reagent, the trifluoromethanesulfonic anhydride and the dimethyl sulfoxide in a molar ratio of (1-5): (1-2.5): (2-3): 2 react inan organic solvent at the reaction temperature of 25-100 DEG C for 6-20 hours to obtain the compound with the structural general formula (I). The reagents used in the method are low in toxicity and environmentally friendly, and use of precious metal catalysts high in price and toxicity is avoided. The reagents trifluoromethanesulfonic anhydride (Tf2O) and dimethyl sulfoxide (DMSO) used in the method are low in toxicity and very low in cost, so that the method is green, environment-friendly, high in economy and suitable for large-scale production.
