25627-01-4Relevant academic research and scientific papers
Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates
Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, p. 5342 - 5347 (2021/06/30)
A practical phosphorylation for generating organophosphates and phosphoramidatesviaelectrochemical dehydrogenative cross-coupling of P(O)H compounds with arenols and anilines is disclosed. This method involves using inorganic iodide salts as both redox catalysts and electrolytes in an undivided cell without the addition of oxidants or bases. A preliminary mechanistic study suggests that radicals are not involved in this process. This method is green and eco-friendly and has good functional group tolerance, high yields and broad substrate scope, with the potential for practical synthesis.
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.
Kinetics and mechanism of the anilinolysis of dimethyl and diethyl chloro(thiono)phosphates
Dey, Nilay Kumar,Hoque, Md. Ehtesham Ul,Kim, Chan Kyung,Lee, Bon-Su,Lee, Hai Whang
scheme or table, p. 544 - 548 (2009/04/04)
The deuterium kinetic isotope effects (KIEs) involving deuterated aniline nucleophiles (XC6H4ND2) are reported for the reactions of dimethyl chlorophosphate (1), dimethyl chlorothionophosphate (2), diethyl chlorophosphate
Phosphoric Amides. 5. Acid-Catalyzed Hydrolysis of Dimethyl N-(Alkylphenyl)phosphoramidates
Modro, Tomasz A.,Rijkmans, Bloys P.
, p. 3208 - 3211 (2007/10/02)
Studies of the acid-catalyzed hydrolysis of dimethyl N-(alkylphenyl)phosphoramidates demonstrate that the LFER between observed rates and basicities of the leaving amines is different for meta/para- and for ortho- substituted derivatives (slopes of logobsd vs. pKa are 0.4 and 0.9, respectively).Since the ΔS(excit) values and KSIE determined are approximately constant irrespective of the position of an alkyl group, the observed change in the slope of the rate/basicity plot is discussed in terms of the steric effects on solvation rather than as an indication of the change in reaction mechanism.
