5573-42-2Relevant academic research and scientific papers
Bu4NI-Catalyzed Dehydrogenative Coupling of Diaryl Phosphinic Acids with C(sp3)-H Bonds of Arenes
Xiong, Biquan,Wang, Gang,Zhou, Congshan,Liu, Yu,Zhang, Panliang,Tang, Kewen
, p. 993 - 999 (2018)
An efficient phosphorylation of C(sp3)-H bonds of arenes with diaryl phosphinic acids via Bu4NI-catalyzed dehydrogenative coupling has been developed. This transformation proceeds efficiently under transition-metal-free reaction conditions and represents a straightforward method to prepare valuable organophosphorus compounds from readily available arenes and diaryl phosphinic acids.
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.
O-Phosphination of Aldehydes/Ketones toward Phosphoric Esters: Experimental and Mechanistic Studies
Qian, Yanyan,Dai, Qiang,Li, Zhiming,Liu, Yu,Zhang, Junliang
, p. 4742 - 4748 (2020/06/29)
Addition of P-H species to carbonyl groups, namely the Pudovik reaction, normally delivers hydroxyl phosphorus compounds, along with phosphate byproducts in some cases. A few controllable systems starting from phosphites were set up to mainly provide the phosphates. Herein, we present a highly selective protocol starting from phosphonate precursors leading to phosphinate derivatives. Enantioenriched phosphinates were successfully achieved from chiral phosphine oxide precursors. Experimental and theoretical investigations were conducted to understand the mechanistic details.
Method for preparing organic phosphate compound by taking P (O)- OH compound and methyl-substituted aromatic hydrocarbon
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Paragraph 0030-0040, (2020/07/29)
The invention provides a high-efficiency and high-selectivity synthetic method for organic phosphate derivatives containing different substituted functional groups. The method uses tetrabutylammoniumiodide as a catalyst and uses a P(O)-OH-containing compound and a methyl-containing aromatic hydrocarbon compound as reaction substrates, and an organic solvent and an oxidant are added in the reaction system. The method has the advantages that the catalyst is cheap and easy to obtain, the substrate applicability is high, the reaction conditions are mild, safe and reliable, the selectivity of an obtained target product is close to 100%, and the yield is up to 90% or more. The method solves shortages in traditional organic phosphate ester compound synthetic methods that reaction selectivity ispoor, reaction steps are complicated, the yield is low, environmentally-harmful agents are used and the like, and has better industrial application prospects. The invention also provides the corresponding organic phosphate derivatives containing the different substituted functional groups.
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).
Novel method for preparing phosphonate through oxidative dehydrogenation coupled reaction of copper-catalyzed diarylphosphine oxide and alcohol
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Paragraph 0016, (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 0262-0266, (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.
Synthesis method of copper-catalyzed phosphate mixed ester compound
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Paragraph 0141-0143, (2019/10/17)
The invention provides a synthesis method of a copper-catalyzed phosphate mixed ester compound. The synthesis method comprises the steps that a phosphate ester azide compound and fatty alcohol are mixed, then a copper catalyst is added, alkali is added, reaction is conducted at the temperature of 20-100 DEG C for 3-24 h, and the phosphate mixed ester compound is obtained through aftertreatment. According to the synthesis method, the phosphate ester azide compound and the fatty alcohol are adopted to synthesize the phosphate mixed ester compound for the first time, in the synthesis process, only the copper catalyst and the alkali with the catalytic dosage are needed to be added, operation is easy, the defect of needing inert gas protection is overcome, and the synthesis method is novel andefficient.
Cetyltrimethyl ammonium bromide catalysed oxidative cross dehydrogenative coupling of benzylic C(sp3)-H bonds in methylarenes with P(O)-OH compounds
Li, Hang,Lei, Jian,Liu, Yongping,Chen, Yi,Au, Chak-Tong,Yin, Shuang-Feng
, p. 302 - 308 (2019/01/10)
An efficient metal-free method for the synthesis of organophosphorus compounds via oxidative cross dehydrogenative coupling of benzylic C(sp3)-H bonds in methylarenes with P(O)-OH compounds catalysed by cetyltrimethyl ammonium bromide (CTAB) is
