19259-70-2Relevant articles and documents
Visible light induced hydrophosphinylation of unactivated alkenes catalyzed by salicylaldehyde
Cao, Peng,Chen, Tian,Fan, Jiaye,Hu, Ping,Li, Miaomiao,Li, Qianggen,Li, Yang,Wang, Bi-Qin,Wang, Simin,Xiong, Fuying,Yuan, Zeqin
supporting information, p. 3600 - 3606 (2021/06/06)
An air and water insensitive visible light induced hydrophosphinylation of unactivated alkenes is reported. A small amount of a simple and cheap compound, salicylaldehyde, is used as a photosensitizer. The reaction is carried out in a basic aqueous solution which enables the deprotonated salicylaldehyde to show visible light absorption.
Palladium-catalyzed C(sp3)–P(III) bond formation reaction with acylphosphines as phosphorus source
Zhang, Mengyue,Ma, Zhichao,Du, Hongguang,Wang, Zhiqian
, (2020/06/29)
Palladium-catalyzed C(sp3)–P(III) bond formation reaction for alkyl substituted phosphines preparation was developed. In this reaction, various alkyl bromides and limited alkyl chlorides reacted with acylphosphine under relative mild and easily accessible condition, and differential phosphines were afforded in good yields. This reaction made up the application of palladium catalysis in C(sp3)–P(III) bond formation, and indicated a practical application of acylphosphine as a phosphination reagent.
Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action
Lyubina, Anna P.,Mironov, Vladimir F.,Pashirova, Tatiana N.,Sapunova, Anastasiia S.,Shaihutdinova, Zukhra M.,Tatarinov, Dmitry A.,Terekhova, Natalia V.,Voloshina, Alexandra D.,Zakharova, Lucia Ya.
, (2020/05/19)
Here we report the synthesis and biological evaluation of a series of new 2-hydroxybenzylphosphonium salts (QPS) with antimicrobial and antitumor dual action. The most active compounds exhibit antimicrobial activity at a micromolar level against Gram-positive bacteria Sa (ATCC 209p and clinical isolates), Bc (1–2 μM) and fungi Tm and Ca, and induced no notable hemolysis at MIC. The change in nature of substituents of the same length led to a drastic change of biological activity. Self-assembly behavior of the octadecyl and oleyl derivatives was studied. QPS demonstrated self-assembly within the micromolar range with the formation of nanosized aggregates capable of the solubilizing hydrophobic probe. The synthesized phosphonium salts were tested for cytotoxicity. The most potent salt was active against on M?Hela cell line with IC50 on the level of doxorubicin and good selectivity. According to the cytofluorimetry analysis, the salts induced mitochondria-dependent apoptosis.
Potassium carbonate promoted nucleophilic addition of alkenes with phosphites
Huang, Zhenjun,Liu, Wei,Li, Sen,Yang, Yutian,Guo, Shengmei,Cai, Hu
supporting information, p. 1295 - 1297 (2020/08/21)
A facile hydrophosphonylation of alkenes by phosphites promoted by potassium carbonate was developed. The reaction features include easy handling, environmental friendliness, and avoidance of the use of strong bases. A variety of alkenes are tolerated in this reaction, with moderate to excellent yields.
Preparation method of alkyl phosphorylated substances
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Paragraph 0023, (2019/10/04)
The invention discloses a preparation method of alkyl phosphorylated substances. According to the invention, alkyl carboxylic acid is used as a starting material, and raw materials are easy to obtain and are various in types. Products prepared by the method disclosed by the invention are various in types and wide in application; and a part of the products can be prepared into important phosphorus ligands and drug key intermediates through simple reduction. In addition, use of high-toxicity phosphine reagents is avoided in the method, the reaction conditions are mild, operation is simple, the yield of the target product is high, pollution is small, and the reaction operation and post-treatment processes are simple, so that the method is suitable for industrial production.
Visible light-promoted metal-free aerobic oxyphosphorylation of olefins: A facile approach to β-ketophosphine oxides
Shi, Yun,Chen, Rongshun,Guo, Kang,Meng, Fei,Cao, Shujun,Gu, Chen,Zhu, Yingguang
supporting information, p. 2062 - 2065 (2018/04/30)
A metal-free direct aerobic oxyphosphorylation of alkenes with H-phosphine oxides has been developed utilizing visible light photoredox catalysis. A variety of β-ketophosphine oxides have been obtained in good yields from simple olefins under air with ine
Stereocontrolled C(sp3)-P bond formation with non-activated alkyl halides and tosylates
Yang, Chu-Ting,Han, Jun,Liu, Jun,Li, Yi,Zhang, Fan,Gu, Mei,Hu, Sheng,Wang, Xiaolin
, p. 24652 - 24656 (2017/07/11)
The C(sp3)-P bond is formed via the reaction between P-H compounds and non-activated alkyl electrophiles, especially secondary alkyl halides and tosylates. This reaction proceeds via an SN2 mechanism with inversion of configuration, so it can be used to form C-P bonds with stereocontrol from chiral secondary alcohols.
Direct conversion of phosphonates to phosphine oxides: An improved synthetic route to phosphines including the first synthesis of methyl JohnPhos
Kendall, Alexander J.,Salazar, Chase A.,Martino, Patrick F.,Tyler, David R.
supporting information, p. 6171 - 6178 (2015/02/19)
The synthesis of tertiary phosphine oxides from phosphonates was achieved reliably and in good to excellent yields using stoichiometric amounts of alkyl or aryl Grignard reagents and sodium trifluoromethanesulfonate (NaOTf). In the absence of the NaOTf additive, covalent coordination oligomers of magnesium and phosphorus species dominate the reaction, producing very low yields of phosphine oxide, but high conversions of the phosphonate starting material. Mechanistic studies revealed that a five-coordinate phosphorus species - not a phosphinate - is the reaction intermediate. A diverse array of phosphonates was converted to phosphine oxides using a variety of Grignard reagents for direct carbon-phosphorus functionalization. This new methodology especially simplifies the synthesis of dimethylphosphino (RPMe2)-type phosphines by using air-, water-, and silica-stable intermediates. To highlight this reaction, a new Buchwald-type ligand ([1,1′-biphenyl]-2-yldimethylphosphine, or methyl JohnPhos) and a classic bidentate phosphine, bis(diphenylphosphino)propane (dppp), were synthesized in excellent yields.
Synthesis of phosphane oxides and phosphonates by cerium-mediated addition of organolithium compounds to chloro-phosphorus compounds
Dalpozzo, Renato,De Nino, Antonio,Miele, Daniela,Tagarelli, Antonio,Bartoli, Giuseppe
, p. 2299 - 2301 (2007/10/03)
The addition of organocerium reagents 2a-g to phosphinoyl chloride 1a or chlorophosphates 1b leads to the synthesis of phosphane oxides 3aa-ag and phosphonates 3bb, be in good to high yield. The reaction can be extended to cerium enolates 4 (of ketones) and 6 (of nitriles) except when a benzyl group bound to the carbonyl moiety should be metallated. The latter reaction is the first reported synthesis of β-oxophosphane oxides by a simple reaction between enolates and a phosphorus(V) halide.
Control over absolute (R,S), relative (syn,anti) and geometrical (E,Z) stereochemistry in the synthesis of allylically substituted alkenes from diphenylphosphinoyl epoxy alcohols
Clayden, Jonathan,McElroy, Andrew B.,Warren, Stuart
, p. 1913 - 1934 (2007/10/02)
Regioselective ring-openings of epoxy alcohols bearing a diphenylphosphinoyl (Ph2PO) group give diols which can undergo stereospecific Horner-Wittig elimination.This method was used to make allylic alcohols, unsaturated β-hydroxy sulfides, homoallylic alcohols and unsaturated amino acids, with control over their absolute (R,S), relative (syn,anti) and geometrical (E,Z) stereochemistry.
