- Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates
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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.
- Xu, Pan,Zhong, Zijian,Zhou, Aihua
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supporting information
p. 5342 - 5347
(2021/06/30)
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- LiI/TBHP Mediated Oxidative Cross-Coupling of P(O)–H Compounds with Phenols and Various Nucleophiles: Direct Access to the Synthesis of Organophosphates
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An efficient and mild method for the direct phosphorylation of phenols, alcohols, and amines with P(O)–H has been reported by LiI/TBHP mediated oxidative cross-coupling reaction. Moreover, this protocol extended to β-keto esters for the synthesis of enol phosphates using H-phosphonates. Notably, this developed method applied for the synthesis of organopesticides such as paraoxon, cyanophos, and methyl parathion. The key features of this protocol are mild conditions, short reaction time, good functional group tolerance, and broad substrate scope.
- Anitha, Thippani,Ashalu, Kashamalla Chinna,Sandeep, Mummadi,Mohd, Aabid,Wencel-Delord, Joanna,Colobert, Francoise,Reddy, Kallu Rajender
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p. 7463 - 7474
(2019/12/03)
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- Organophotocatalytic Synthesis of Phosphoramidates
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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.
- Meazza, Marta,Kowalczuk, Agnieszka,Shirley, Luke,Yang, Jung Woon,Guo, Hao,Rios, Ramon
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p. 719 - 723
(2016/03/09)
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- 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
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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.
- Kaboudin, Babak,Kazemi, Foad,Habibi, Fereshteh
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supporting information
p. 6364 - 6367
(2015/11/16)
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- An efficient and convenient procedure for the one-pot synthesis of α-aminophosphonates from aryl azides under solvent-free conditions
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A novel and simple approach to the multicomponent one-pot reaction of aldehydes, diethyl phosphite, and azides to form α-aminophosphonates under solvent-free conditions at room temperature has been developed. In the presence of iodine and iron, aryl azides were, for the first time, used as substrates for the synthesis of α-aminophosphonates. The reactions were completed within 5 minutes to 12 hours and afforded the corresponding products in good yields.
- Yu, Ya-Qin
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p. 2545 - 2550
(2013/09/24)
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- Practical and reliable synthesis of dialkyl N-arylphosphoramidates with nitroarenes as substrates
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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.
- Haggam, Reda,Conrad, Jürgen,Beifuss, Uwe
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scheme or table
p. 6627 - 6630
(2010/03/01)
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- Kinetics and mechanism of the anilinolysis of dimethyl and diethyl chloro(thiono)phosphates
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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
- Dey, Nilay Kumar,Hoque, Md. Ehtesham Ul,Kim, Chan Kyung,Lee, Bon-Su,Lee, Hai Whang
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scheme or table
p. 544 - 548
(2009/04/04)
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- A New Approach to the Atherton-Todd Reaction
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N-Arylphosphoramidates 4 are prepared by reacting formanilides 1 and chloroacetanilides 1' with diethyl phosphite under phase-transfer conditions.
- Lukanov, L. K.,Venkov, A. P.,Mollov, N. M.
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p. 971 - 973
(2007/10/02)
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