- DCC-assisted direct esterification of phosphinic and phosphoric acids with O-nucleophiles
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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.
- Xiong, Biquan,Wang, Gang,Zhou, Congshan,Liu, Yu,Li, Jiandong,Zhang, Pangliang,Tang, Kewen
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- Pseudohalogenation of phosphites
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A new type of Atherton-Todd reaction for a convenient pseudohalogenation of phosphites has been developed. Direct azidation, cyanation, and thiocyanation of (RO)2P(O)H (R = Et, i-Bu, Ph) were accomplished readily with sodium pseudohalides in acetonitrile under mild modified Atherton-Todd conditions. The corresponding phosphorochloridates were demonstrated by GC/MS to be the intermediates. Pseudohalogenations of ethyl phenylphosphinate and diphenylphosphine oxide were also investigated.
- Shi, Enxue,Pei, Chengxin
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- Hydrolysis and alcoholysis of phosphinates and phosphonates
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Phosphinic and phosphonic acids useful intermediates and biologically active compounds may be prepared from their esters: phosphinates and phosphonates, respectively, by acid-catalyzed hydrolysis either on conventional heating or on MW irradiation. The transesterification of alkyl phosphinates took place only in the presence of suitable ionic liquids as the catalysts. In the cases of phenylphosphonates, depending on the nature of the ionic liquid, the formation of the ester was accompanied by the fission of the C–O bond.
- Harsági, Nikoletta,Keglevich, Gy?rgy,Sz?ll?si, Betti,Varga, Petra Regina
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- Manganese-Catalyzed and Mediated Synthesis of Arylphosphinates and Related Compounds
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The free-radical arylation of H-phosphinates and related compounds was examined. A practical catalytic process with the air as the oxidant could not be found. However, an inexpensive and robust methodology was developed, using catalytic Mn(II) as the radi
- Berger, Olivier,Montchamp, Jean-Luc
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p. 9239 - 9256
(2019/08/12)
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- Electrochemical Dehydrogenative Phosphorylation of Alcohols for the Synthesis of Organophosphinates
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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
- Deng, Lingling,Wang, Yang,Mei, Haibo,Pan, Yi,Han, Jianlin
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p. 949 - 956
(2019/01/14)
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- Method for preparing organophosphate compound from P(O)-OH-containing compound and alcohol through efficient esterification
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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.
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Paragraph 0025
(2017/07/21)
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- Manganese-Mediated Intermolecular Arylation of H-Phosphinates and Related Compounds
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The intermolecular radical functionalization of arenes with aryl and alkyl H-phosphinate esters, as well as diphenylphosphine oxide and H-phosphonate diesters, is described. The novel catalytic MnII/excess MnIVsystem is a convenient
- Berger, Olivier,Montchamp, Jean-Luc
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supporting information
p. 12385 - 12388
(2015/02/19)
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- A "green" variation of the Hirao reaction: The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates and secondary phosphine oxides with bromoarenes using a P-ligand-free Pd(OAc)2 catalyst under microwave and solvent-free conditions
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The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates, diphenylphosphine oxide and dialkylphosphine oxides with bromoarenes may be performed in the presence of a P-ligand-free Pd(OAc)2 catalyst and triethylamine under microwave-assisted (MW) and, in almost all cases, solvent-free conditions to afford diethyl arylphosphonates, alkyl diphenylphosphinates, aryldiphenylphosphine oxides and dialkylphenylphosphine oxides, respectively. This is the "greenest" accomplishment of the well-known Hirao reaction that has now been found to have general application for a broad spectrum of >P(O)H species with different reactivity and a great variety of substituted bromobenzenes. The alkyl phenyl-H-phosphinates were prepared by the MW-promoted alkylation of phenyl-H-phosphinic acid in the absence of any solvent. This journal is the Partner Organisations 2014.
- Keglevich, Gyoergy,Jablonkai, Erzsebet,Balazs, Laszlo B.
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p. 22808 - 22816
(2014/06/23)
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