3389-73-9Relevant academic research and scientific papers
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.
Preparation method of compound containing P-O bond or P-S bond
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Paragraph 0207-0211, (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.
Selective Substitution of POCl 3 with Organometallic Reagents: Synthesis of Phosphinates and Phosphonates
Verbelen, Bram,Dehaen, Wim,Binnemans, Koen
, p. 2019 - 2026 (2018/04/14)
The selectivity of the substitution reaction of phosphoryl chloride with organometallic reagents was investigated using NMR spectroscopy. This led to the discovery that the selectivity of the substitution reaction can be tuned by choosing a proper organometallic reagent. A phosphinate could be obtained by using a Grignard reagent whereas an organozinc reagent provided a phosphonate. Based on these results, one-pot synthetic methods for the preparation of phosphinates and phosphonates using commercially available starting materials were developed. Both methods allow the synthesis of a broad range of either phosphinate or phosphonate derivatives in a straightforward and general procedure. Moreover, using these one-pot procedures, mixed systems substituted with different alkyl/aryl groups can be prepared.
Method for synthesis of organophosphorus compound by photo-induced iodine catalyzed Atherton-Todd reaction
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Paragraph 0015, (2018/12/14)
The invention belongs to the technical field of organic synthesis, discloses a method for synthesis of organophosphorus compound by photo-induced iodine catalyzed Atherton-Todd reaction. The method comprises the following steps: a compound shown as formula II and a nucleophilic reagent are subjected to reaction for 24 hours in a dichloromethane solvent, an oxygen atmosphere, under irradiation condition of room temperature and the action of a halogenated reagent I2, then the organophosphorus compound shown as the formula II is obtained through washing, drying, separating and purifying. According to the the method provided by the invention, compared with traditional Atherton-Todd reaction, no catalysis of metal is needed,no addition of alkali is needed, reaction environment such as metal, high temperature and strong base is replaced, a series of organophosphorus compounds can be synthesized by catalyzing a variety of substrates under the irradiation condition of room temperature, and hasthe advantages of good universality, short reaction time and higher yield.
Base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides
Xiong, Biquan,Ye, Qianqian,Feng, Xiaofeng,Zhu, Longzhi,Chen, Tieqiao,Zhou, Yongbo,Au, Chak-Tong,Yin, Shuang-Feng
, p. 9057 - 9063 (2015/03/05)
A novel base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides has been developed. The protocol is practical, representing a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. A plausible mechanism was proposed for this reaction.
Influence of Additions of Salts with Stable Anions on Ethyl Diphenylphosphinylacetate Alkylation
Yarkevich, A. N.,Smolina, E. V.,Novikova, O. V.,Tsvetkov, E. N.
, p. 553 - 558 (2007/10/03)
The influence of the addition of LiClO4, Mg(ClO4)2, ans NaI, salts capable of forming complexes with electron donor centers, on the direction of Ph2P(O)CH2COOEt interphase alkylation with alkyl halides RHlg in the presence of K2CO3 and Cs2CO3 was studied.Depending on the reaction conditions mixtures with various ratios of Ph2P(O)CH2COOEt, Ph2P(O)OR, and Ph2P(O)CH2COOR were obtained upon the alkylation.The formation of these compounds can be envisioned respectively as alkylation by the methylene fragment, by phosphoryl oxygen with subsequent destruction of intermediate phosphinomethylene, and by carbonyl oxygen with further stabilization of the resulting acetal via splitting off of the lowest of the alkoxy groups.
