19315-13-0Relevant academic research and scientific papers
Organic compounds, organic semiconductor layer and organic electronic device
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Paragraph 0430-0435, (2020/05/29)
The present invention relates to a compound according to formula 1:suitable for use as a layer material for electronic devices, and to an organic semiconductor layer comprising at least one compound according to formula 1, as well as to an organic electronic device comprising at least one organic semiconductor layer, and a method of manufacturing the same.
Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)?H Compounds
Tan, Chen,Liu, Xinyuan,Jia, Huanxin,Zhao, Xiaowen,Chen, Jian,Wang, Zhiyong,Tan, Jiajing
supporting information, p. 881 - 887 (2020/01/02)
Herein, we report a highly efficient ZnI2-triggered oxidative cross-coupling reaction of P(O)?H compounds and amines. This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time. Besides, the reaction proceeds under mild conditions, which avoids the use of hazardous reagents, and is applicable to scale-up syntheses as well as late-stage functionalization of drug molecules. The stereospecific coupling is also achieved from readily available optically enriched P(O)?H compounds.
Evaluation and development of methodologies for the synthesis of thiophosphinic acids
Winters, Karen R.,Montchamp, Jean-Luc
, p. 14545 - 14558 (2020/12/29)
Thiophosphorus acids R1R2P(S)OH constitute an important class of organophosphorus compounds, in which the phosphorus atom is intrinsically chiral if R1 ≠ R2. In connection with a project aimed at the preparation of chiral thiophosphorus acids, various available literature methods were considered, but few fit the requirement of odorless reagents. Herein, the results of our studies on the synthesis of thiophosphinic acids are reported. Ultimately, two major approaches were selected: (1) the Stec reaction of phosphorus amides with carbon disulfide; and (2) the one-pot synthesis of thiophosphorus acids from H-phosphinates, an organometallic nucleophile, and quenching with elemental sulfur. An application to the preparation of a potential chiral phosphorus organocatalyst is also reported.
Ni-Catalyzed Asymmetric Allylation of Secondary Phosphine Oxides
Liu, Xu-Teng,Zhang, Ya-Qian,Han, Xue-Yu,Sun, Shi-Ping,Zhang, Qing-Wei
supporting information, p. 16584 - 16589 (2019/10/21)
A nickel-catalyzed asymmetric allylation of secondary phosphine oxides (SPO) for the synthesis of tertiary phosphine oxides (TPO) was realized with high enantioselectivity. The dynamic kinetic asymmetric transformation of SPO was accomplished in the prese
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
H-adamantylphosphinates as universal precursors of P-stereogenic compounds
Gatineau, David,Nguyen, Duc Hanh,Hérault, Damien,Vanthuyne, Nicolas,Leclaire, Julien,Giordano, Laurent,Buono, Gérard
, p. 4132 - 4141 (2015/05/05)
A new family of H-adamantylphosphinates as universal precursors of P-stereogenic ligands was obtained in one step from commercial chlorophosphines. Both enantiomers of these air- and moisture-stable intermediates can easily be separated by semipreparative chiral HPLC on a gram scale and individually undergo stereoselective transformations to afford each enantiomer of a set of P-stereogenic compounds such as secondary phosphine oxides and boron-protected monophosphines.
Palladium-catalyzed phosphonylation: Synthesis of C3-, C4-, and C5-phosphonylated pyrazoles
Tran, Gael,Pardo, Domingo Gomez,Tsuchiya, Tomoki,Hillebrand, Stefan,Vors, Jean-Pierre,Cossy, Janine
supporting information, p. 5550 - 5553 (2013/11/19)
A palladium-catalyzed cross-coupling between 3-, 4-, and 5-halo-pyrazoles and H-phosphonates, H-phosphinates, and secondary phosphine oxides has been developed. This coupling reaction constitutes the first general method allowing the introduction of a gre
Simple unprecedented conversion of phosphine oxides and sulfides to phosphine boranes using sodium borohydride
Rajendran, Kamalraj V.,Gilheany, Declan G.
supporting information; experimental part, 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.
Room temperature, palladium-mediated P-arylation of secondary phosphine oxides
Bloomfield, Aaron J.,Herzon, Seth B.
supporting information, p. 4370 - 4373 (2012/10/29)
We show that a broad range of aryl iodides are efficiently coupled with secondary phosphine oxides using 1 mol % of a catalyst formed in situ from tris(dibenzylideneacetone)dipalladium and Xantphos (1). Scalemic (S)-methylphenylphosphine oxide [(S)-2e] is shown to undergo arylation without detectable stereoerosion. The application of this method to the synthesis of novel P-chiral phosphines and PCP ligands is demonstrated.
Sodium in liquid ammonia - A versatile tool in modifications of arylphosphine oxides
Stankevi?, Marek,W?odarczyk, Adam,Jaklińska, Magdalena,Parcheta, Renata,Pietrusiewicz, K. Micha?
experimental part, p. 8671 - 8678 (2011/12/03)
A simple and practical method for modifications of tertiary arylphosphine oxides based on their reaction with sodium in liquid ammonia is presented. Depending on the structure of the starting compounds, either dearomatisation of the phenyl substituent or cleavage of a P-aryl bond from phosphorus atom can be selectively performed and the corresponding (1,4-cyclohexadien-3-yl)phosphine oxides or secondary phosphine oxides were obtained in good to excellent yields.
