62056-94-4Relevant academic research and scientific papers
Redox-Neutral P(O)-N Coupling between P(O)-H Compounds and Azides via Dual Copper and Photoredox Catalysis
Wu, Yanan,Chen, Ken,Ge, Xia,Ma, Panpan,Xu, Zhiyuan,Lu, Hongjian,Li, Guigen
supporting information, p. 6143 - 6149 (2020/07/30)
We report a redox-neutral P(O)-N coupling reaction of P(O)-H compounds with azides via photoredox and copper catalysis, providing new access to useful phosphinamides, phosphonamides, and phosphoramides. This transformation tolerates a wide range of nucleophilic functionalities including alcohol and amine nucleophiles, which makes up for the deficiency of classical nitrogen nucleophilic substitution reactions. As a demonstration of the broad potential applications of this new methodology, late-stage functionalization of a diverse array of azido-bearing natural products and drug molecules, a preliminary asymmetric reaction, and a continuous visible-light photoflow process have been developed.
Synthesis of new organophosphorus compounds using the atherton-todd reaction as a versatile tool
Wagner, Sebastian,Rakotomalala, Muriel,Bykov, Yana,Walter, Olaf,Doering, Manfred
scheme or table, p. 216 - 222 (2012/07/13)
This article discusses the behavior of seven organophosphorus compounds under Atherton-Todd conditions. Therefore, the reactivity and selectivity of different (phen)oxaphosphinines, dioxaphosphinines, dioxaphosphinanes, and diphenylphosphine oxide with three nucleophiles were systematically studied. The results prove the versatility of the Atherton-Todd reaction to a broad range of organophosphorus compounds with different phosphorus environments and reactive Pi-H bonds. The nucleophiles studied in this article were chosen as model substrates for amines and alcohols. Because organophosphorus molecules are important and versatile compounds, for a broad field of applications, novel synthetic approaches are of interest to both academia and industry. As an example, the single-step synthesis of the bridged 1,3-phenylene bis(diphenylphosphinate) with potential flame-retardant properties was added to this study. In addition, the reaction is utilized for the synthesis of a novel organophosphorus anhydride.
Organic phosphorus compounds 106.1 a 31P-NMR study of phosphinous-, phosphinic-, and thiophosphinic amides
Maier, Ludwig,Diel, Peter J.
, p. 273 - 300 (2007/10/03)
The synthesis, physical, chemical and spectroscopic properties of eight different types of phosphinous-, phosphinic-and thiophosphinic amides are reported. It is shown that the 31P-chem. shifts of tertiary amides are at lower magnetic field than that of secondary amides. As an exception, in the bis(tertiary butyl) series this trend is reversed.
Evaluation of Phosphinic Acid Derivatives as Reagents For Amine Protection in Peptide Synthesis
Ramage, Robert,Atrash, Butrus,Hopton, David,Parrot, Maxwell J.
, p. 1217 - 1226 (2007/10/02)
The results of a kinetic study of the acid-catalysed methanolysis of a series of N-(2-phenyl-ethyl)phosphinamides incorporating selected substituents on phosphorus have been evaluated in order to define the optimum reagent and conditions for amine protection of α-amino acids during peptide synthesis.
