98976-30-8Relevant academic research and scientific papers
Copper(I)-induced sulfenylation of H-phosphonates, H-phosphonites and phosphine oxides with aryl/alkylsulfonylhydrazides as a thiol surrogate
Kumaraswamy, Gullapalli,Raju, Ragam
, p. 2591 - 2598 (2014)
Aerobic dehydrogenative sulfenylation of H-phosphonites, and phosphine oxides with aryl/alkylsulfonyl hydrazides catalyzed by a sub-stoichiometric amount of copper iodide has been accomplished. This protocol is compatible with functional groups, and results in various thiophosphate derivatives in good to high yields.
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.
supporting information, 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
Iridium versus Iridium: Nanocluster and Monometallic Catalysts Carrying the Same Ligand Behave Differently
Cano, Israel,Martínez-Prieto, Luis M.,Chaudret, Bruno,van Leeuwen, Piet W. N. M.
, p. 1444 - 1450 (2017/02/05)
A specific secondary phosphine oxide (SPO) ligand (tert-butyl(phenyl)phosphine oxide) was employed to generate two iridium catalysts, an Ir–SPO complex and IrNPs (iridium nanoparticles) ligated with SPO ligands, which were compared mutually and with several supported iridium catalysts with the aim to establish the differences in their catalytic properties. The Ir–SPO-based catalysts showed totally different activities and selectivities in the hydrogenation of various substituted aldehydes, in which H2is likely cleaved by a metal–ligand cooperation, that is, the SPO ligand and a neighboring metal centre operate in tandem to activate the hydrogen molecule. In addition, the supported IrNPs behave very differently from both Ir–SPO catalysts. This study exemplifies perfectly the advantages and disadvantages related to the use of the main types of catalysts, and thus the dissimilarities between them.
General and Stereoselective Method for the Synthesis of Sterically Congested and Structurally Diverse P-Stereogenic Secondary Phosphine Oxides
Han, Zhengxu S.,Wu, Hao,Xu, Yibo,Zhang, Yongda,Qu, Bo,Li, Zhibin,Caldwell, Donald R.,Fandrick, Keith R.,Zhang, Li,Roschangar, Frank,Song, Jinhua J.,Senanayake, Chris H.
supporting information, p. 1796 - 1799 (2017/04/11)
A general and efficient method for the synthesis of bulky and structurally diverse P-stereogenic chiral secondary phosphine oxides (SPOs) by using readily available chiral amino alcohol templates is described. These chiral SPOs could be used as chiral building blocks for the synthesis of difficult-to-access bulky P-stereogenic phosphine compounds or ligands for organic catalysis.
Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines
Beaud, Rodolphe,Phipps, Robert J.,Gaunt, Matthew J.
supporting information, p. 13183 - 13186 (2016/10/22)
Catalytic synthesis of nonracemic P-chiral phosphine derivatives remains a significant challenge. Here we report Cu-catalyzed enantioselective arylation of secondary phosphine oxides with diaryliodonium salts for the synthesis of tertiary phosphine oxides
Simple unprecedented conversion of phosphine oxides and sulfides to phosphine boranes using sodium borohydride
Rajendran, Kamalraj V.,Gilheany, Declan G.
supporting information; scheme or table, p. 817 - 819 (2012/02/03)
A variety of phosphine oxides and sulfides can be efficiently converted directly to the corresponding phosphine boranes using oxalyl chloride followed by sodium borohydride. Optically active P-stereogenic phosphine oxides can be converted stereospecifically to phosphine boranes with inversion of configuration by treatment with Meerwein's salt followed by sodium borohydride.
Stereoselective addition of grignard reagents to new P-chirogenic N-phosphinoylbenzaldimines: Effect of the phosphorus substituents on the stereoselectivity
Notar Francesco, Irene,Egloff, Coraline,Wagner, Alain,Colobert, Francoise
scheme or table, p. 4037 - 4045 (2011/09/15)
Several phosphinoylimines have been synthesized in five steps by starting from the appropriate phosphane oxide and were then treated with methylmagnesium bromide to give both diastereoisomers in high yields and with promising diastereomeric ratios. Then N-[(tert-butyl)(phenyl)phosphinoyl]benzaldimine, which displayed the best results, was subjected to the 1,2-addition of various Grignard reagents to evaluate the best chiral induction due to the stereogenic phosphorus atom. The corresponding adducts were obtained in excellent yields and with moderate to excellent diastereoisomeric ratios. Copyright
Steric control in the synthesis of phosphinous acid-coordinated mono- and binuclear platinum(II) complexes
Achard, Thierry,Giordano, Laurent,Tenaglia, Alphonse,Gimbert, Yves,Buono, Gerard
scheme or table, p. 3936 - 3950 (2010/12/25)
Several phosphinous acid-coordinated platinum complexes were prepared and characterized. In the presence of secondary phosphine oxide (2 equiv), PtCl 2(cod) was converted to a series of cis/trans platinum complexes PtCl2[R1R2POH]2 featuring phosphinous acids (PAs) as ligands (20-29). A balance between the steric and electronic effects of ligands governs their coordination mode. NMR experiments and density functional theory calculations show that the anti conformer for trans complexes is favored by intramolecular HCl bonding. PtCl 2[R1R2POH]2 treated with NEt 3 (1 equiv) gave bimetallic platinum complexes cis-[Pt 2(μ-Cl)2{(R1R2PO) 2H}2] characterized by 31P NMR and X-ray diffraction. An unusual monometallic platinum complex, cis-[PtCl 2{(i-Bu)2PO}2H]-[HNEt 3]+ (30), was isolated and characterized as a possible intermediate in the formation of dinuclear species. Silver acetate and triethylamine both reacted with PtCl2[(t-Bu)2POH] 2 to yield new bulky Pt(κ2-acetato){[(t-Bu) 2PO]2H} platinum complex 31. The structure of complexes 20d (R1 = Ph, R2 = Cy), 21 (R1 = Ph, R 2 = t-Bu), 21d (R1 = Ph, R2 = t-Bu), 24 (R 1 = R2 = t-Bu), 25 (R1 = R2 = Cy), 30 (R1 = R2 = i-Bu), and 31 (R1 = R2 = t-Bu) were determined by X-ray diffraction.
Stereoselective addition of Grignard reagents to new P-chirogenic N-phosphinoylimines
Francesco, Irene Notar,Wagner, Alain,Colobert, Francoise
scheme or table, p. 2139 - 2141 (2010/07/04)
The addition of various Grignard reagents to P-t-butyl-P-phenyl-N- phosphinoyl benzaldimine provides a stereoselective method for the synthesis of chiral phosphinoylamines. The Royal Society of Chemistry.
New look into the synthesis of polyhalogenoarylphosphanes
Nycz, Jacek E.
experimental part, p. 2605 - 2612 (2010/08/06)
The present study shows new aspects of the synthesis of polyhalogenoarylphosphanes. The sterically hindered anions Ph(R)P-Y- (1a-c, Y = O, lone pair; R = Ph, But) have been used to show the complexity of the reaction between phosphorus nucleophiles and hexahalogenobenzenes or 9-bromofluorene (E3). The Ph(But)P-O-(1a) anion reacts with hexachlorobenzene (E1), hexafluorobenzene (E2), or E3 to give Ph(R)P(O)X (4a-c, X = F, Cl, Br) with the release of the corresponding carbanion as a nucleofuge, followed by side reactions. In contrast, the lithium phosphides Ph(R)PLi (1b,c) react with hexahalogenobenzenes to give the corresponding diphosphanes 5a,b as the main product and traces of P-arylated products, i.e., Ph(R)P-C6X 5 (10a,b, X = Cl, F). Unexpectedly, Ph(But)PLi (1b) reacts with an excess of 9-bromofluorene to give only halogenophosphane Ph(Bu t)P-X. Taylor & Francis Group, LLC.
