1135-98-4Relevant academic research and scientific papers
Examining Trichloroisocyanuric Acid and Oxalyl Chloride in Complementary Approaches to Fluorination of Group 15 Heteroatoms
Bornemann, Dustin,Brüning, Fabian,Bartalucci, Niccolò,Wettstein, Lionel,Pitts, Cody Ross
, (2021)
A mild, oxidative fluorination approach to a variety of fluorinated phosphorus compounds using trichloroisocyanuric acid (TCICA) and KF was developed as a complement to a recent study on deoxygenative fluorination using oxalyl chloride. Herein, the syntheses of several fluorinated organophosphorus compounds are reported, and both TCICA/KF and oxalyl chloride/KF conditions are compared and contrasted throughout. Initial investigations of the method on other group 15 heteroatoms (i. e., As, Sb, and Bi) are also reported, with varied success. This work notably extends the known TCICA/KF reactivity series to another group of elements beyond previously studied chalcogens (S, Se, and Te) and halogens (iodine) and expands the utility of the previously reported oxalyl chloride/KF method.
THE FLUORINATION OF HYDROPHOSPHORYL COMPOUNDS USING 2-HYDROPERFLUOROPROPYL AZIDE
Lermontov, S. A.,popov, A. V.,Sukhozhenko, I. I.,Pushin, A. N.,Martynov, I. V.
, p. 839 - 841 (1990)
2-Hydroperfluoropropyl azide efficiently fluorinates hydrophosphoryl compounds to give the corresponding P(V) acid fluorides.
Deoxyfluorination of Carboxylic, Sulfonic, Phosphinic Acids and Phosphine Oxides by Perfluoroalkyl Ether Carboxylic Acids Featuring CF2O Units
Zhao, Shiyu,Guo, Yong,Su, Zhaoben,Wu, Chengying,Chen, Wei,Chen, Qing-Yun
, p. 1225 - 1232 (2021)
The deoxyfluorination of carboxylic, sulfonic, phosphinic acids and phosphine oxides is a fundamentally important approach to access acyl fluorides, sulfonyl fluorides and phosphoric fluorides, thus the development of inexpensive, stable, easy-to-handle, versatile, and efficient deoxyfluorination reagents is highly desired. Herein, we report the use of potassium salts of perfluoroalkyl ether carboxylic acids (PFECA) featuring CF2O units as deoxyfluorination reagents, which are generated mainly as by-products in the manufacture of hexafluoropropene oxide (HFPO). The synthesis of acyl fluorides, sulfonyl fluorides and phosphoric fluorides can be realized via carbonic difluoride (COF2) generated in situ from thermal degradation of the PFECA salt.
Fluorination of phosphorus(+3) derivatives by xenon difluoride
Lermontov, S. A.,Popov, A. V.,Zavorin, S. I.,Sukhojenko, I. I.,Kuryleva, N. V.,et al.
, p. 233 - 236 (1994)
Xenon difluoride, XeF2, effectively fluorinates various phosphorous acid derivatives as well as hydrophosphoryl compounds.Arbuzov rearrangement is followed by i-Bu --> t-Bu isomerization in the case of i-BuOPF2.
TFAA/DMSO-Promoted Fluorination of P(O)?H and P(O)?OH Compounds: Compatible Access to Fluorophosphonates and Phosphonofluoridates
Li, Qi-Wei,Zhang, Xin-Yue,Lu, Lu,Wu, Zi-Qian,Li, Ji,Li, Gui-Zhi,Sun, Kai,Yang, Shang-Dong,Yang, Bin
supporting information, p. 938 - 946 (2022/02/07)
A TFAA/DMSO/NaF-based system for the efficient fluorination of P(O)?H and P(O)?OH compounds has been developed. Without adding highly toxic and expensive fluorination reagents, this novel transformation provides direct and compatible access to a variety o
Preparation method of phosphoryl fluoride compound
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Paragraph 0044-0047, (2021/11/03)
The invention discloses a preparation method of a phosphoryl fluoride compound. The invention uses the phosphorus reagent under the protection of inert gas. Sodium fluoride is used as a starting raw material, and trifluoroacetic anhydride and dimethyl sul
Fluorination method
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Paragraph 0169-0212; 0215-0268, (2021/01/12)
In order to overcome the problems of high cost and low stability of the existing fluorination reagents for preparing acyl fluoride, sulfonyl fluoride and phosphoryl fluoride compounds, the invention provides a fluorination method, which comprises the following operation steps of: adding a fluorination reagent into a substrate, wherein the fluorination reagent comprises cations M and anions, the anions are selected from one or more of perfluoropolyether chain carboxylic acid anions as shown in the specification: CF3(OCF2)nCO2, wherein n is selected from 1-10; the substrate comprises a carboxylic acid compound, a sulfonic acid compound, a phosphoric acid compound and a phosphine oxide compound; and carrying out fluorination reaction to obtain acyl fluoride, sulfonyl fluoride and phosphoryl fluoride products. According to the fluorination method provided by the invention, the perfluoropolyether chain carboxylate is used as a fluorination reagent, so that the dehydroxylation fluorination reaction of the carboxylic acid compound, the sulfonic acid compound and the phosphoric acid compound and the fluorination reaction of the phosphine oxide compound are realized, the product yield isrelatively high, and the fluorination method has relatively good universality for different substrates.
Direct, oxidative halogenation of diaryl- or dialkylphosphine oxides with (dihaloiodo)arenes
Eljo, Jasmin,Murphy, Graham K.
supporting information, p. 2965 - 2969 (2018/06/30)
The oxidative halogenation of diaryl- or dialkylphosphine oxides with the hypervalent iodine reagents (difluoroiodo)toluene (p-TolIF2, 1) and (dichloroiodo)benzene (PhICl2, 2) is reported. Phosphoric fluorides could be recovered in 32–75% yield, or they could be trapped with EtOH to give the corresponding phosphinate in typically good yield. Phosphoric chlorides were not readily isolable, and were trapped with alcohol and amine nucleophiles, giving diaryl- or dialkylphos-phinates and phosphinamides in up to 90% yield.
Electrophilic Fluorination of Secondary Phosphine Oxides and Its Application to P-O Bond Construction
Chen, Qian,Zeng, Jiekun,Yan, Xinxing,Huang, Yulin,Wen, Chunxiao,Liu, Xingguo,Zhang, Kun
, p. 10043 - 10048 (2016/11/02)
A novel and efficient electrophilic fluorination of secondary phosphine oxides with Selectfluor has been achieved. This transformation provides direct access to phosphoric fluorides in up to 92% yield under mild conditions. In addition, P-O bond construction via a one-pot coupling process of secondary phosphine oxides with water or alcohols in the presence of Selectfluor leads to the formation of phosphinic acids or phosphinates in up to 96% yield.
Copper-promoted oxidative-fluorination of arylphosphine under mild conditions
Liu, Na,Mao, Liu-Liang,Yang, Bin,Yang, Shang-Dong
supporting information, p. 10879 - 10882 (2014/10/15)
An efficient method for the synthesis of phosphoric fluoride via oxidative coupling between hydrophosphine oxide and NaF is reported. DDQ serves as the oxidizing reagent as well as the hydrogen acceptor. The process involves a Cu(ii) catalysis and exhibits great functional group tolerance under mild reaction conditions. the Partner Organisations 2014.
