83470-30-8Relevant academic research and scientific papers
Novel method for preparing phosphonate through oxidative dehydrogenation coupled reaction of copper-catalyzed diarylphosphine oxide and alcohol
-
Paragraph 0018, (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.
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.).
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
-
Paragraph 0040, (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.
Direct aerobic oxidative esterification and arylation of P(O)-OH compounds with alcohols and diaryliodonium triflates
Xiong, Biquan,Feng, Xiaofeng,Zhu, Longzhi,Chen, Tieqiao,Zhou, Yongbo,Au, Chak-Tong,Yin, Shuang-Feng
, p. 537 - 543 (2015/04/14)
Copper-catalyzed aerobic oxidative esterification of P(O)-OH compounds is achieved using alcohols as efficient esterification reagents, giving the expected products with good to moderate yields. Furthermore, it is shown that the arylation of P(O)-OH compounds proceeds efficiently to produce the corresponding products via the treatment of diaryliodonium triflates under mild reaction conditions. It is a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. The protocol is convenient for practical application. A plausible mechanism has been proposed for the reaction.
Transposition of the phosphinoyl groups in the base-induced rearrangements of N,O-bis(diarylphosphinoyl)hydroxylamines
Harger, Martin J. P.
, p. 4507 - 4508 (2007/10/03)
Because the N- and O-phosphinoyl groups can change places prior to rearrangement, Ph2P(O)NHOP(O)Ar2 and Ar2P(O)NHOP(O)Ph2 (Ar = p-tolyl) both give mixtures of two phosphonamidic-phosphimic anhydrides, Ph(PhNH)P(O)OP(O)Ar2 and Ar(ArNH)P(O)OP(O)Ph2, on treatment with KOBu(t) in Bu(t)OH. The transposition of the phosphinoyl groups may involve phosphorane intermediates (7 and 9) having the P atom contained within a three-membered ring.
Reactions of 7-methoxyimino-4-methylchromene-2,8-dione with phosphines. Preparation of N-substituted 7-amino-8-hydroxy-4-methyl-2H-[1]-benzopyran-2-ones
Nicolaides, Demetrios N.,Awad, Raed Wajih,Litinas, Konstantinos E.,Malamidou-Xenikaki, Elizabeth
, p. 15007 - 15016 (2007/10/03)
7-Methoxyimino-4-methylchromene-2,8-dione 2 reacts with triarylphosphines 1(a-d) to give the unexpected 7-arylomino-8-hydroxy-4-methyl-2H-[1]-benzopyran-2-ones 7(a-d) and methyl diarylphosphinates 8(a-d) in high yields. The reaction of 2 with trialkylphosphines 1(e,f) as well as with diphenylphosphine 15 leads to the formation of the N-dialkylphosphinoyl derivatives 11, 12, 14 and the N-diphenylphosphinoyl derivative 19, along with compounds 7(e,f). The methylation of compounds 7a, 7f, 11 and 19 is also studied and reaction mechanisms to explain the formation of the products obtained are suggested.
Palladium catalyzed preparation of monoaryl and diarylphosphinates from methyl phosphinate
Lei,Stoakes,Schwabacher
, p. 1255 - 1260 (2007/10/02)
A simple and effective preparation of methyl esters of monoarylphosphinic acids has been developed, which involves palladium catalyzed coupling of aryl iodides with methyl phosphinate in the presence of tertiary amines or propylene oxide (1,2-epoxypropane
