1706-91-8Relevant academic research and scientific papers
A solvent-free method for the preparation of phosphinates from P(O)-OH compounds with alkyl chlorides
Yuan, Huihui,Wang, Mingyue,Fan, Lei,Yang, Jia,Wang, Shuai,Zhong, Hong
supporting information, (2021/11/17)
Herein, a new solvent-free synthetic method using P(O)-OH compound and alkyl chloride for phosphinate compounds is disclosed. This transformation proceeds smoothly under the promotion of a lone base and presents the advantages of an easily available raw material source, a simple post treatment process, good functional group tolerance and high reaction efficiency. Good yield was obtained when the reaction was magnified to gram scale, and the molar ratio of P(O)-OH compounds and alkyl chlorides can be decreased to 1:2. This protocol provides a practical method for the preparation of phosphorus derivatives. Furthermore, the reaction mechanism was explored by means of 31P NMR.
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.
Novel method for preparing phosphonate through oxidative dehydrogenation coupled reaction of copper-catalyzed diarylphosphine oxide and alcohol
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Paragraph 0015, (2020/12/14)
The invention provides a method for efficiently and highly selectively synthesizing phosphonate derivatives containing different substituted functional groups. According to the method, cuprous iodideis used as a catalyst, 2,2'-dipyridyl is used as a ligand, pyridine is used as an alkali, oxygen is used as an oxidant, diarylphosphine oxide and an alcohol compound are used as reaction substrates, and an organic solvent is added into a reaction system. The method has the advantages that the catalyst and the oxidant are cheap and easily available; substrate applicability is high; reaction conditions are mild, safe and reliable; the selectivity of the obtained target products is close to 100%; and the yield of the target products is as high as 90% or above. The method overcomes the defects ofpoor reaction selectivity, complex reaction steps, low yield, need for reagents harmful to the environment and the like in the traditional synthesis of phosphonate derivatives, and has favorable industrial application prospects. The invention also provides the corresponding phosphonate derivatives containing different substituted functional groups.
Preparation method of compound containing P-O bond or P-S bond
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Paragraph 0187-0191, (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.
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).
Electrochemical Dehydrogenative Coupling of Alcohols with Hydrogen Phosphoryl Compounds: A Green Protocol for P?O Bond Formation
Li, Qian-Yu,Swaroop, Toreshettahally R.,Hou, Cheng,Wang, Zi-Qiang,Pan, Ying-Ming,Tang, Hai-Tao
supporting information, p. 1761 - 1765 (2019/02/20)
This study reports the environment-friendly electrochemical transformation of structurally diverse phosphorus compounds and alcohol into phosphonates in the presence of ammonium iodide as electrolyte and redox catalyst in acetonitrile at ambient temperature. This method for P?O bond formation exhibits remarkable features, such as transition metal- and oxidant-free conditions. A reliable mechanism is proposed after control and cyclic voltammetry experiments. (Figure presented.).
A scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with RSH/ROH
Li, Yujun,Yang, Qi,Yang, Liquan,Lei, Ning,Zheng, Ke
supporting information, p. 4981 - 4984 (2019/05/21)
A practical, scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with thiols, phenols and alcohols in both an undivided cell and a continuous-flow setup is disclosed. Its broad substrate scope (>50 examples), good functional-group tolerance and scalability (>10 g) show potential for practical synthesis. A preliminary mechanistic study suggests that the phosphorus radicals are involved in the catalytic cycle.
Electrochemical Dehydrogenative Phosphorylation of Alcohols for the Synthesis of Organophosphinates
Deng, Lingling,Wang, Yang,Mei, Haibo,Pan, Yi,Han, Jianlin
, p. 949 - 956 (2019/01/14)
An eco-friendly and efficient method for the synthesis of organophosphinates via an electrochemical cross-dehydrogenative-coupling reaction between alcohols and secondary phosphine oxides has been developed. This electrochemical reaction was conducted at
DCC-assisted direct esterification of phosphinic and phosphoric acids with O-nucleophiles
Xiong, Biquan,Wang, Gang,Zhou, Congshan,Liu, Yu,Li, Jiandong,Zhang, Pangliang,Tang, Kewen
supporting information, p. 239 - 244 (2017/11/20)
A novel and efficient dicyclohexylcarbodiimide-promoted protocol for the selective and controllable esterification of P(O)OH compounds using O-nucleophiles (alcohols and phenols) as efficient esterification reagents is described. This method features a high efficiency and good functional-group tolerance, meaning a simple way to synthesize a broad spectrum of phosphinic and phosphoric acid esters from basic starting materials with moderate to excellent yields.
Method for preparing organophosphate compound from P(O)-OH-containing compound and alcohol through efficient esterification
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Paragraph 0034, (2017/07/21)
The invention provides a method for efficiently and highly selectively synthesizing an organophosphate derivative containing different substitute functional groups. The method is characterized by adopting a polypeptide catalyst as a condensation reagent, taking a P(O)-OH-containing compound and alcohol as reaction substrates, and adding an organic solvent in a reaction system. The method disclosed by the invention has the advantages that the catalyst is cheap in cost and easy to obtain; the substrate applicability is high; reaction conditions are mild, safe and reliable; the selectivity of an obtained target product is close to 100 percent, and the yield is up to 90 percent or more. According to the method provided by the invention, the defects of a traditional method for synthesizing an organophosphate compound that the reaction selectivity is poor, the reaction steps are tedious, the yield is low, reagents which are harmful to the environment are required to be used, and the like are solved, and a good industrial application prospect is obtained. Meanwhile, the invention also provides the corresponding organophosphate derivative containing different substitute functional groups.
