20809-97-6Relevant articles and documents
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.
Trichloroisocyanuric Acid as an Efficient Reagent for the Synthesis of Phosphoroamidates via Atherton-Todd Reaction under Base-Free Conditions
Kaboudin, Babak,Donyavi, Atousa,Kazemi, Foad
, p. 170 - 174 (2017/09/28)
A simple, efficient, and novel method is developed for the synthesis of phosphoroamidates via an Atherton-Todd coupling reaction of amines with dialkyl H-phosphite using trichloroisocyanuric acid as an efficient and safe reagent. Treatment of amines with dialkyl H-phosphite and trichloroisocyanuric acid under base-free conditions gives phosphoroamidates in moderate to good yields. The reaction proceeded effectively to afford the corresponding phosphoroamidates via a dehydrogenative coupling of H-phosphonates with amines. This method is easy, rapid, and good-yielding for the synthesis of phosphoroamidates.
Organophotocatalytic Synthesis of Phosphoramidates
Meazza, Marta,Kowalczuk, Agnieszka,Shirley, Luke,Yang, Jung Woon,Guo, Hao,Rios, Ramon
, p. 719 - 723 (2016/03/09)
We describe the use of visible light in conjunction with an organic dye for the synthesis of phosphoramidates. Cross dehydrogenative coupling reactions between phosphites and amines are reported using organic dyes and light as catalysts for the first time. It is not only a novel application of organic dyes but also fulfils the requirement of sustainability and green chemistry avoiding the use of chromatographic purification techniques. The product was simply isolated from the reaction mixture via an acid-base work-up procedure, rendering the pure product in good yields.
Fe3O4@MgO nanoparticles as an efficient recyclable catalyst for the synthesis of phosphoroamidates via the Atherton-Todd reaction Dedicated to Professor Tsutomu Yokomatsu from Tokyo University of Pharmacy and Life Sciences on the occasion of his 65th birthday
Kaboudin, Babak,Kazemi, Foad,Habibi, Fereshteh
supporting information, p. 6364 - 6367 (2015/11/16)
A simple and efficient method is presented for the synthesis of phosphoroamidates in moderate to good yield via the Atherton-Todd coupling of primary amines with H-dialkyl phosphites using Fe3O4@MgO nanoparticles as a recyclable catalyst.
Copper-catalyzed aerobic oxidative cross-coupling of arylamines and dialkylphosphites leading to N-arylphosphoramidates
Wang, Gao,Yu, Qing-Ying,Chen, Shan-Yong,Yu, Xiao-Qi
supporting information, p. 6230 - 6232 (2013/10/22)
An efficient method to generate N-P bonds directly from N-H and P-H bonds is described. Various arylamines and dialkylphosphites were directly oxidized to the corresponding N-arylphosphoramidates at room temperature in moderate to good yields by using an inexpensive catalyst-oxidant (CuBr/air) system.
Practical and reliable synthesis of dialkyl N-arylphosphoramidates with nitroarenes as substrates
Haggam, Reda,Conrad, Jürgen,Beifuss, Uwe
scheme or table, p. 6627 - 6630 (2010/03/01)
A new single-step transformation of readily available nitroarenes with trialkyl phosphites, which can be performed both under thermal and microwave conditions, delivers dialkyl N-arylphosphoramidates in good yields and short reaction times.
