42822-64-0Relevant articles and documents
Manganese-Catalyzed and Mediated Synthesis of Arylphosphinates and Related Compounds
Berger, Olivier,Montchamp, Jean-Luc
, p. 9239 - 9256 (2019/08/12)
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
Silver-catalyzed highly regioselective phosphonation of arenes bearing electron-withdrawing groups
Mao, Xuerong,Ma, Xiao,Zhang, Shuwei,Hu, Hongwen,Zhu, Chengjian,Cheng, Yixiang
, p. 4245 - 4248 (2013/07/26)
A highly efficient, AgI/K2S2O 8-mediated regioselective phosphonation reaction has been developed by using electron-deficient directing groups. These phosphonation reactions were performed with N,N-dialkylbenzamides, N,N-dialkylbenzenesulfonamides, and nitrobenzene. This method has a broad substrate scope and offers facile construction of C-P bonds. Copyright
Pd(II)-catalyzed phosphorylation of aryl C-H bonds
Feng, Chen-Guo,Ye, Mengchun,Xiao, Kai-Jiong,Li, Suhua,Yu, Jin-Quan
supporting information, p. 9322 - 9325 (2013/07/19)
A Pd(II)-catalyzed C-H phosphorylation reaction has been developed using heterocycle-directed ortho-palladation. Both H-phosphonates and diaryl phosphine oxides are suitable coupling partners for this reaction.
Design and synthesis of small molecule glycerol 3-phosphate acyltransferase inhibitors
Wydysh, Edward A.,Medghalchi, Susan M.,Vadlamudi, Aravinda,Townsendd, Craig A.
experimental part, p. 3317 - 3327 (2010/03/26)
The incidence of obesity and other diseases associated with an increased triacylglycerol mass is growing rapidly, particularly in the United States. Glycerol 3-phosphate acyltransferase (GPAT) catalyzes the ratelimiting step of glycerolipid biosynthesis, the acylation of glycerol 3-phosphate with saturated long-chain acyl-CoAs. In an effort to produce small molecule inhibitors of this enzyme, a series of benzoic and phosphonic acids was designed and synthesized. In vitro testing of this series has led to the identification of several compounds, in particular 2-(nonylsulfonamido)benzoic acid (15g), possessing moderate GPAT inhibitory activity in an intact mitochondrial assay.
Synthesis of 1H-1,3-benzazaphospholes: Substituent influence and mechanistical aspects
Heinicke, Joachim,Gupta, Nidhi,Surana, Anushka,Peulecke, Normen,Witt, Brigitte,Steinhauser, Kinga,Bansal, Raj K,Jones, Peter G
, p. 9963 - 9972 (2007/10/03)
Various substituted carboxylic acid 2-chloro- and 2-bromoanilides 1a-j react with triethylphosphite in the presence of anhydrous NiCl2 or NiBr2 to give o-acylamido-benzenephosphonic acid esters 2a-g and 2j. Yields depend strongly on the substituents. 2-Fluoro-4,6-dibromoacetanilide 1g reacts only at 6-position, indicating an o-directed process. Based on substituent effects, we infer a mechanism via Ni(0) intermediates that insert into the carbon-halogen bond. The N-tertiary 2-bromoformanilide 4 does not undergo phosphonylation to 5 in the presence of the Ni-catalyst but reacts in the presence of Pd-catalysts. The subsequent reduction of the N-secondary o-acylamido-benzenephosphonic acid esters 2 with excess LiAlH4 is coupled with an intramolecular cyclisation to the 1H-1,3-benzazaphospholes 6 whereas the N-tertiary derivative 5 does not undergo cyclisation upon reduction. NMR data and the crystal structure of 6d are reported.
Intramolecular Hydrogen-bond Participation in Phosphonylammonium Salt Formation
Smith III, Amos B.,Ducry, Laurent,Corbett, R. Michael,Hirschmann, Ralph
, p. 3887 - 3890 (2007/10/03)
equation presented A series of phosphonochloridates and phosphonyl dichlorides were prepared, and their reactivity with triethylamine has been investigated using 31P NMR spectroscopy. Taken together these studies provide evidence that an intram
1H-1,3-benzazaphospholes: The organometallic route and a new three-step synthesis with reductive ring closure
Bansal, Raj K.,Gupta, Neelima,Heinicke, Joachim,Nikonov, George N.,Saguitova, Farida,Sharma, Dinesh C.
, p. 264 - 269 (2007/10/03)
Primary and N-secondary 2-phosphanylanilines were synthesized via metallation of 2-bromoanilines, coupling with CIP(NMe2)2, alcoholysis and reduction with LiAlH4, and subsequently reacted with formimidoester hydrochloride to give 1,3-benzazaphospholes. For 1H-1,3-benzazaphospholes, a shorter alternative three-step synthesis was developed, based on N-acylation of 2-bromoaniline, NiCl2-catalyzed arylation of triethyl phosphite and a new reductive cyclization of amidophosphonic acid ester with excess LiAlH4.
OXIDATIVE PHOSPHONYLATION OF AROMATIC COMPOUNDS
Effenberger, Franz,Kottmann, Hariolf
, p. 4171 - 4182 (2007/10/02)
Aryl phosphonates can be prepared in good yield from the respective arenes and tri- or dialkylphosphites by either chemical or anodic oxidation.The anodic oxidation proceeds either via phosphinium radical cations, which then attack the arenes electrophilically, or via arene radical cations, which add the trialkylphosphite as nucleophile.Aryl phosphonates are also obtained in good yield by chemical oxidation with peroxodisulfate/AgNO3 in acetonitrile/water or glacial acetic acid.The diethylphosphinium radical cation, formed from diethylphosphite by oxidation with Ag(II), is supposed to be the reactive species in this process.Raising the silver salt concentration leads to an increase in polyphosphonylation.Selectivity ratios were determined for the oxidative phosphonylation process.
