7282-98-6Relevant academic research and scientific papers
Gold-Catalyzed Access to Isophosphinoline 2-Oxides
Ayad, Tahar,Boosaliki, Hooriye,Burilov, Alexander R.,Chacktas, Geraud,Darvish, Fatemeh,Hariri, Mina,Lebibi, Jacques,Mengue Me Ndong, Karen-Pacelye,Mwande-Maguene, Gabin,Pirat, Jean-Luc,Sechet, Nora,Tran Do, Minh Loan,Virieux, David
, p. 7813 - 7824 (2021/06/25)
Gold(I)-catalyzed reactions of electron-poor alkynes are still a challenging process. A straightforward synthesis of phosphorus-based heterocycles, namely, 2-phenyl 1H-isophosphinoline 2-oxides 1, is reported. The reaction used PPh3AuCl precatalyst in com
Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids
Ash, Jeffrey,Cordero, Paula,Huang, Hai,Kang, Jun Yong
, p. 6007 - 6014 (2021/07/21)
An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.
Desymmetrization of Phosphinic Acids via Pd-Catalyzed Asymmetric Allylic Alkylation: Rapid Access to P-Chiral Phosphinates
Trost, Barry M.,Spohr, Simon M.,Rolka, Alessa B.,Kalnmals, Christopher A.
, p. 14098 - 14103 (2019/10/11)
The synthesis of P-chiral compounds is challenging, especially since useful catalytic methods for preparing such molecules are scarce. Herein we disclose a desymmetrization that employs phosphinic acids as prochiral nucleophiles in a Pd-catalyzed asymmetr
Practical synthesis of chiral vinylphosphine oxides by direct nucleophilic substitution. Stereodivergent synthesis of aminophosphine ligands
Oliana, Marco,King, Frank,Horton, Peter N.,Hursthouse,Hii, King Kuok
, p. 2472 - 2479 (2007/10/03)
A practical synthesis of optically pure alkylphenylvinylphosphine oxides is described, utilizing a nucleophilic displacement at phosphorus to install the vinyl moiety. The products were used to prepare classes of P-stereogenic aminophosphine (PN) and aminohydroxyphosphine (PNO) ligands. Stereocontrol can be exerted at various stages of the synthesis, to provide specific combinations of chirality in the final product. The effect of the stereogenic phosphorus and match-mismatch of chiralities of PNO ligands were examined in the asymmetric ruthenium-catalyzed hydrogen transfer reduction of three aryl ketones.
Pallado-catalysed P-arylations and P-vinylation of 2-hydrogeno-2-oxo-1,4,2- oxazaphosphinanes
Pirat, Jean-Luc,Monbrun, Jér?me,Virieux, David,Cristau, Henri-Jean
, p. 7029 - 7036 (2007/10/03)
A simple and effective preparation of 2-aryl- (or 2-vinyl)-1,4,2- oxazaphosphinanes, phosphorus analogues of aryl-morpholinols has been developed, involving palladium catalysed coupling of aryl (or vinyl)-halides with 2-H-1,4,2-oxazaphosphinane in presenc
Facile synthesis of functionalised phenylphosphinic acid derivatives
Boyd, E. Andrew,Boyd, Mark E.K.,Loh Jr., Vincent M.
, p. 1651 - 1654 (2007/10/03)
Functionalised phenylphosphinic acid derivatives have been synthesised by addition of bis(trimethylsilyl)phenylphosphinite 2 to a series of electrophiles.
Nucleophilic Substitution in Benzylic Thiophosphinyl and Thiophosphonyl Chlorides: the Contribution of Elimination-Addition Pathways with Methylenethiooxophosphorane (Thiophosphene) Intermediates
Coogan, Michael P.,Harger, Martin J. P.
, p. 2101 - 2108 (2007/10/02)
For the reactions of ArCH2P(S)(Ph)Cl and ArCH2P(S)(NMe2)Cl with Et2NH, changing ArCH2 from benzyl to 4-nitrobenzyl increases the rates of substitution by factors of 80 and >103, respectively, and reduces markedly the ability to discriminate bet
Kinetic Study on the Alkaline Hydrolysis of Some Tetracoordinate PV Esters of 2,4-Dinitrophenol
Cevasco, Giorgio,Thea, Sergio
, p. 1103 - 1106 (2007/10/02)
The alkaline hydrolysis of 2,4-dinitrophenyl esters of benzylphosphinic, benzylphosphonic and benzylphosphonamidic acid does not proceed through a carbanion-promoted dissociative mechanism, a possible alternative pathway to the usual SN2(P) process; this is a further indication of the clear preference for associative displacement at phosphorous.
PHOSPHORORGANISCHE VERBINDUNGEN 120. VERSUCHE ZUM NACHWEIS VON "PHOSPHENEN" AUS GEEIGNETEN PHOSPHINSAEUREDERIVATEN DURCH ELIMINIERUNG
Weidert, Peter J.,Geyer, Ekkehard,Horner, Leopold
, p. 55 - 60 (2007/10/02)
Phosphinicacidhalogenides with the structure C are reacted with strong bases in the presence of carbonylcompounds.The eventually as intermediates formed "phosphenes" lead with carbonyl compounds to olefines following the course of the "PO-activated olefination".The intermediates don't react with olefines (stilbene or cyclopentadiene) to an isolable adduct.Key words: Phosphinicacidhalides; phosphenes as intermediates; PO-activated olefination; synthesis of olefines.
Organophosphorus Compounds. XIX. Synthesis of 2,3-Dihydro-1H-1,2-benzazaphosphole 2-Oxides, Variously Substituted on Nitrogen and Phosphorus, by N-P Cyclization of Zwitterionic Intermediates
Collins, David J.,Drygala, Peter F.,Swan, John M.
, p. 2517 - 2536 (2007/10/02)
2-Phenyl-2,3-dihydro-1H-1,2-benzazaphosphole 2-oxide (7a) was prepared by thermolysis of the corresponding zwitterionic amino phosphinic acid (4), or its hydrochloride salt (1).Thermolysis of methyl (2-aminobenzyl)phenylphosphinate (5a) was accompanied by intermolecu;ar O->N transmethylation to give, after cyclization, 1-methyl-2-phenyl-2,3-dihydro-1H-1,2-benzazaphosphole 2-oxide (9a); similarly, the ethyl ester (5b) gave the N-ethyl heterocycle (9b). Reaction of 2-phthalimidobenzyl bromide (13a) with diethyl methylphosphonite (14b) gave ethyl (2-phthalimidobenzyl)methylphosphinate 15a).Hydrolysis of (15a) afforded (2-aminobenzyl)-methylphosphinic acid (16), and thermolysis of this produced 2-methyl-2,3-dihydro-1H-1,2-benzazaphosphole 2-oxide (18a). 1-Methyl-2-methoxy-2,3-dihydro-1H-1,2-benzazaphosphole 2-oxide (24) was synthesized in an analogous manner. Base catalyzed N-alkylation of the benzazaphosphole derivatives (7a) and (18a) was readily achieved, and the interconversion of 2-oxides and 2-sulfides was accomplished by conventional methods.
