- Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics
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We presented a palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins, which utilize H-phosphinates and secondary phosphine oxides as the phosphine sources, respectively. A variety of phosphorylated heteroaromatics were obtained in m
- Chen, Chen,Ding, Jie,Liu, Liying,Huang, Yujie,Zhu, Bolin
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supporting information
p. 200 - 205
(2021/10/29)
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- Microwave-assisted esterification of P-acids
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The possibilities for the preparation of dialky phenylphosphonates were evaluated. On the one hand, the oxidation of phenyl-H-phosphinates gave the corresponding phenylphosphonic acid monoesters. On the other hand, phenylphosphonates may be prepared by MW-assisted direct esterification of phenylphosphonic acid. The reaction with alcohols was performed under MW irradiation in the presence of an ionic liquid as the catalyst. The second ester function was established by alkylating esterification carried out with alkyl halides in the presence of triethylamine under MW conditions.
- ábrányi-Balogh, Péter,Harsági, Nikoletta,Keglevich, Gy?rgy,Kiss, Nóra Zsuzsa
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- Nickel-Catalyzed Electrosynthesis of Aryl and Vinyl Phosphinates
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A mild and useful nickel-catalyzed electrochemical phosphonylation of aryl and vinyl bromides is described. We show that alkyl H-phenylphosphinates can be coupled electrochemically with functionalized aryl and vinyl bromides using very simple conditions (Fe/Ni anode, bench-stable nickel pre-catalyst, undivided cell, galvanostatic electrolysis) to furnish the corresponding aryl and vinyl phosphinates in satisfactory to good yields. Couplings can also be applied to heteroaromatic bromides with some limitations like increased propensity to hydro-dehalogenation.
- Daili, Farah,Ouarti, Abdelhakim,Pinaud, Marine,Kribii, Ibtihal,Sengmany, Stéphane,Le Gall, Erwan,Léonel, Eric
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supporting information
p. 3452 - 3455
(2020/05/25)
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- Continuous flow esterification of a H-phosphinic acid, and transesterification of H-phosphinates and H-phosphonates under microwave conditions
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The microwave (MW)-assisted direct esterification of phenyl-H-phosphinic acid, transesterification of the alkyl phenyl-H-phosphinates so obtained, and the similar reaction of dibenzyl phosphite (DBP) were investigated in detail, and the batch accomplishme
- Henyecz, Réka,Keglevich, Gy?rgy,Kiss, Nóra Zsuzsa
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- Silver-promoted cascade radical cyclization of γ,δ-unsaturated oxime esters with P(O)H compounds: synthesis of phosphorylated pyrrolines
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A cascade radical cyclization was realized for the first silver-promoted imino-phosphorylation of γ,δ-unsaturated oxime esters, which provided a step-economical and redox-neutral route to access a variety of phosphorylated pyrrolines in good to excellent yields. Moreover, a new bulky trivalent phosphine ligand with a pyrroline motif was obtained through a deoxidation process.
- Chen, Chen,Bao, Yinwei,Zhao, Jinghui,Zhu, Bolin
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supporting information
p. 14697 - 14700
(2019/12/11)
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- Synthesis of P(O)-S organophosphorus compounds by dehydrogenative coupling reaction of P(O)H compounds with aryl thiols in the presence of base and air
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The synthesis method of P(O)-S organophosphorus compounds by dehydrogenative coupling reaction of P(O)H compounds and aryl thiols was developed. The reaction was carried in the presence of a base and air, and exhibited good characters such as metal-free,
- He, Wei,Hou, Xiao,Li, Xinjin,Song, Liang,Yu, Qing,Wang, Zhongwei
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supporting information
p. 3133 - 3138
(2017/05/08)
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- Direct synthesis of thiophosphates by reaction of diphenylphosphine oxide with sulfonyl chlorides
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A new method for the synthesis of thiophosphates by reductive coupling reaction of diphenylphosphine oxide and sulfonyl chlorides has been developed. The reaction is metal-free and needs no additives, affording various aryl and alkyl substituted thiophosphates in good to excellent yields under mild conditions.
- He, Wei,Wang, Zhiming,Li, Xinjin,Yu, Qing,Wang, Zhongwei
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supporting information
p. 7594 - 7598
(2016/11/11)
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- Synthesis of alkyl α-aminomethyl-phenylphosphinates and N,N-bis(alkoxyphenylphosphinylmethyl)amines by the microwave-assisted Kabachnik–Fields reaction
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As a novel extension, the Kabachnik–Fields reaction was applied to the synthesis of alkyl α-aminomethyl-phenylphosphinates, and the double phospha-Mannich reaction was utilized in the preparation of bis(alkoxyphenylphosphinylmethyl)amines. A total of 27 new aminophosphinate derivatives were synthesized by the microwave-assisted solvent-free condensation of alkyl phenyl-H-phosphinates, paraformaldehyde, and primary or secondary amines. The starting P-species were also prepared under microwave conditions. The formation of the N-methylated aminomethyl-phenylphosphinate by-products was also investigated.
- Bálint, Erika,Tóth, Regina Eszter,Keglevich, Gy?rgy
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p. 323 - 335
(2016/10/11)
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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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- T3P-assisted esterification and amidation of phosphinic acids
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A few phosphinic acids, such as phenylphosphinic acids, 1-hydroxy-3-phospholene 1-oxides and 1-hydroxyphospholane oxides are esterified with simple alcohols in the presence of propylphosphonic anhydride (T3P). If 1.1 equiv of the T3P reagent is used, the esterifications are fast and efficient at 25° C. In the case of more reactive models it was enough to apply 0.66 equiv of T3P at 85°C under microwave conditions. The amidation of 1-hydroxy-3-methyl-3-phospholene oxide could also be accomplished under similar conditions.
- Jablonkai, Erzsébet,Henyecz, Réka,Milen, Mátyás,Kóti, János,Keglevich, Gy?rgy
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p. 8280 - 8285
(2015/03/05)
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- Chemistry of the versatile (hydroxymethyl)phosphinyl P(O)CH2OH functional group
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(Hydroxymethyl)phosphorus compounds are well-known and valuable compounds in general; however the use of (hydroxymethyl)phosphinates R1P(O) (OR2)CH2OH in particular has been much more limited. The potential of this functio
- Berger, Olivier,Gavara, Laurent,Montchamp, Jean-Luc
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supporting information; experimental part
p. 3404 - 3407
(2012/09/08)
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- Microwave-assisted esterification of phosphinic acids by alcohols, phenols, and alkyl halogenides
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Cyclic phosphinic acids undergo direct esterification with alcohols at ca. 200°C under microwave conditions. Copyright Taylor & Francis Group, LLC.
- Keglevich, Gyoergy,Kiss, Nora Z.,Balint, Erika,Jablonkai, Erzsebet,Gruen, Alajos,Milen, Matyas,Frigyes, David,Gre, Istvan
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body text
p. 802 - 803
(2011/06/25)
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- Novel synthesis of phosphinates by the microwave-assisted esterification of phosphinic acids
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1-Hydroxy-3-phospholene oxides (1 and 3) and phenyl-H-phosphinic acid (6) are converted to the corresponding phosphinic esters (2, 4, and 7, respectively) by reaction with simple alcohols on microwave irradiation. Under traditional heating conditions, the
- Kiss, Nora Zsuzsa,Ludanyi, Krisztina,Drahos, Laszlo,Keglevich, Gyoergy
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experimental part
p. 2392 - 2404
(2009/12/03)
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- Palladium-catalyzed phosphorus-carbon bond formation: Cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates
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The direct formation of H-arylphosphinates and related compounds can be accomplished using palladium catalysis. This full paper examines the scope and some mechanistic aspects of this phosphorus-carbon bond forming reaction. The reactions of alkenyl and allylic halides are also described for the first time. This novel cross-coupling provides a convenient access to a variety of substituted H-phosphinates.
- Bravo-Altamirano, Karla,Huang, Zhihong,Montchamp, Jean-Luc
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p. 6315 - 6329
(2007/10/03)
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- Recent advances in phosphorus-carbon bond formation: Synthesis of H-phosphinic acid derivatives from hypophosphorous compounds
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This account summarizes the research conducted in our laboratory over the past five years. New methodologies were devised for the formation of P-C bonds with a focus on the reactions of hypophosphorous acid derivatives. Three types of reactions have been developed: palladium-catalyzed cross-coupling, room-temperature radical addition, and palladium-catalyzed addition. Our results are summarized in each of these areas and include some of our most recent data. (1) Our palladium-catalyzed cross-coupling has been extended to the direct coupling of alkyl phosphinates with a variety of aryl, heteroaryl, and even alkenyl electrophiles. (2) The addition of sodium hypophosphite under radical conditions is extended from alkenes to alkynes. (3) The catalytic addition of hypophosphorous compounds using palladium catalysts (hydrophosphinylation) is also discussed.
- Montchamp, Jean-Luc
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p. 2388 - 2406
(2007/10/03)
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- A novel and convenient preparation of hypophosphite esters
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Only a few methods have been described for the preparation of hypophosphite esters (alkyl phosphinates, ROP(O)H2). As a result, comparatively few applications have been reported, and these intermediates have not been widely exploited in organop
- Deprèle, Sylvine,Montchamp, Jean-Luc
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p. 154 - 163
(2007/10/03)
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- Orthosilicate-mediated esterification of monosubstituted phosphinic acids
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(matrix presented) Monosubstituted phosphinic acids are esterified with orthosilicates in excellent yields. Phosphinylidene-containing acids react selectively under these conditions, while disubstituted phosphinic acids and phosphonic acids remain unchanged. One-pot procedures are also described for the preparation of phosphinate esters from an alcohol. This novel method provides a convenient and general alternative to more commonly employed conditions such as diazomethane or carbodiimide.
- Dumond, Yves R.,Baker, Rhonda L.,Montchamp, Jean-Luc
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p. 3341 - 3344
(2007/10/03)
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- Syntheses and Investigations of isoindol-9b(2H)-yl>phosphinates and -phosphonates: a New Class of Heterocycles
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We attempted to synthesize diethyl (1-methyl-2-phthalimidoethyl)phosphonate (14a) in a Michaelis-Becker reaction using diethyl sodiophosphonate (13) and the tosylate 12a of (2-hydroxypropyl)phthalimide as starting materials.Instead of TsO substitution in
- Neidlein, Richard,Greulich, Peter,Kramer, Walter
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p. 2407 - 2417
(2007/10/02)
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