Fe3O4@MgO nanoparticles as an efficient recyclable catalyst for the synthesis of phosphoroamidates via the Atherton–Todd reaction

Kaboudin, Babak; Kazemi, Foad; Habibi, Fereshteh

doi:10.1016/j.tetlet.2015.09.129

Cited by 17 publications

(7 citation statements)

References 59 publications

(5 reference statements)

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“…In 2015, Fe 3 O 4 @MgO nanoparticles were used as a catalyst to synthesize P-N from primary amines and H-P via the Atherton-Todd coupling reaction with CCl 4 ( Table 1, route c) [105]. After column chromatography (on silica), P-Ns were isolated in 52-85% yield.…”

Section: Using Transition Metal Catalystsmentioning

confidence: 99%

“…In the Fe 3 O 4 @MgO nanoparticle-mediated synthesis of P-Ns as per the procedure reported by Habibi et al [ 105 ], the mechanism involves the formation of the (RO) 2 P(O)Cl ( d ACP; R = alkyl) intermediate from the reaction of dialkyl H-phosphonate ((OR) 2 P(O)H, R = alkyl) with CCl 4 ( Scheme 28 ). Following, the amine in the presence of Fe 3 O 4 @MgO nanoparticles couples with the d ACP by nucleophilic substitution to give the P-N product, eliminating HCl.…”

Section: Mechanistic Considerationsmentioning

confidence: 99%

“…In the Fe 3 O 4 @MgO nanoparticle-mediated synthesis of P-Ns as per the procedure reported by Habibi et al [105], the mechanism involves the formation of the ( oxidized to form the Cu(III)-amine-phosphonate complex, which undergoes reductive elimination of the copper catalyst to yield the desired P-N. Although this mechanism seems plausible, it could not easily explain the formation of the side products.…”

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confidence: 99%

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Opening up the Toolbox: Synthesis and Mechanisms of Phosphoramidates

2020

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This review covers the main synthetic routes to and the corresponding mechanisms of phosphoramidate formation. The synthetic routes can be separated into six categories: salt elimination, oxidative cross-coupling, azide, reduction, hydrophosphinylation, and phosphoramidate-aldehyde-dienophile (PAD). Examples of some important compounds synthesized through these routes are provided. As an important class of organophosphorus compounds, the applications of phosphoramidate compounds, are also briefly introduced.

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Section: Using Transition Metal Catalystsmentioning

confidence: 99%

Section: Mechanistic Considerationsmentioning

confidence: 99%

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confidence: 99%

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Opening up the Toolbox: Synthesis and Mechanisms of Phosphoramidates

2020

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“…Одним из наиболее перспективных методов синтеза амидофосфатов является реакция Атертона-Тодда: взаимодействие гидрофосфорильных соединений с различными аминами в четыреххлористом углероде в разных экспериментальных условиях (Corre, 2014) . Известны работы по фосфорилированию аминов, их гидрохлоридов, с использованием в качестве катализаторов тетраалкиламмоний бромидов (Zwierzak, 1984) , а использование наночастиц Fe 3 O 4 @MgO (Kaboudin, 2015) , трихлоризоциануровой кислоты (Kaboudin, 2018) в качестве эффективных реагентов, также позволяет существенно повысить выход целевых продуктов реакции. В настоящее время в литературе имеются всего две публикации по синтезу диалкиламидофосфатов с использованием микроволнового облучения (Milen, 2014) .…”

Section: Introductionunclassified

Synthesis, Molecular and Crystal Structures of Tetraethyl 1,3-Phenylenebis (Phosphoramidate) and Tetrapropyl 1,3-Phenylenebis (Phosphoramidate)

Kuandykova,

Dzhiembaev,

Dobrynin

et al. 2024

SCT

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doctor of chemistry, professor, academician of NAS RK, president of NAS RK, general director of JSC "Institute of fuel, catalysis and electrochemistry named after D.V. Sokolsky (Almaty, Kazakhstan) H = 4 Editorial board: ADEKENOV Sergazy Mynzhasarovich (deputy editor-in-chief) doctor of chemical sciences, professor, academician of NAS RK, director of the international Scientific and production holding «Phytochemistry» (Karaganda, Kazakhstan) H = 11 AGABEKOV Vladimir Enokovich (deputy editor-in-chief), doctor of chemistry, professor, academician of NAS of Belarus, honorary director of the Institute of Chemistry of new materials (Minsk, Belarus) H = 13 STRNAD Miroslav, head of the laboratory of the institute of Experimental Botany of the Czech academy of sciences, professor (Olomouc, Czech Republic) H = 66 BURKITBAYEV Mukhambetkali, doctor of chemistry, professor, academician of NAS RK, first vice-rector of al-Farabi KazNU (Almaty, Kazakhstan) H = 11 HOHMANN Judith, head of the department of pharmacognosy, faculty of Pharmacy, university of Szeged, director of the interdisciplinary center for Life sciences (Szeged, ungary) H = 38 ROSS Samir, Ph.D, professor, school of Pharmacy, national center for scientific research of Herbal Products, University of Mississippi (Oxford, USA) H = 35 KHUTORYANSKY Vitaly, Ph.D, pharmacist, professor at the University of Reading (Reading, England) H = 40 TELTAYEV Bagdat Burkhanbayuly, doctor of technical sciences, professor, corresponding member of NAS RK, ministry of Industry and infrastructure development of the Republic of Kazakhstan (Almaty, Kazakhstan) H = 13 PHARUK Asana Dar, professor at Hamdard al-Majid college of Oriental medicine. faculty of Oriental medicine, Hamdard university (Karachi, Pakistan) H = 21 FAZYLOV Serik Drakhmetovich, doctor of chemistry, professor, academician of NAS RK, deputy director for institute of Organic synthesis and coal chemistry (Karaganda, Kazakhstan) H = 6 ZHOROBEKOVA Sharipa Zhorobekovna, doctor of chemistry, professor, academician of NAS of Kyrgyzstan, Institute of Chemistry and chemical technology of NAS KR (Bishkek, Kyrgyzstan) H = 4 KHALIKOV Jurabay Khalikovich, doctor of chemistry, professor, academician of the academy of sciences of tajikistan, institute of Chemistry named after V.I. Nikitin AS RT (Tajikistan) H = 6 FARZALIEV Vagif Medzhid ogly, doctor of chemistry, professor, academician of NAS of Azerbaijan (Azerbaijan) H = 13 GARELIK Hemda, PhD in chemistry, president of the department of Chemistry and Environment of the International Union of Pure and Applied Chemistry (London, England) H = 15 News of the National Academy of Sciences of the Republic of Kazakhstan. Series of chemistry and technology.

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“…Recently, direct functionalization of the P(O)–H bond to construct the P(O)–N bond was proven to be an efficient pathway for the synthesis of organophosphorus compounds with the advantages of high atom and step economy . As useful synthetic strategies, various new direct P(O)–N bond formation methodologies are emerging through the P(O)–N cross-coupling process, including photocatalyzed oxidation, electrochemical oxidation, transition-metal-catalyzed oxidation, I 2 -catalyzed oxidation, Tf 2 O-promoted activating strategy, diselenide-mediated catalysis, Atherton–Todd reaction, and so on. Organic hydrazines are a class of highly versatile and easily accessible coupling partners in organic synthesis .…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Phosphorylation of N,N-Disubstituted Hydrazines: Synthesis of Multisubstituted Phosphorylhydrazides as Potential Anticancer Agents

et al. 2022

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An efficient copper-catalyzed aerobic oxidative cross-dehydrogenative coupling reaction for the synthesis of multisubstituted phosphorylhydrazides from N,N-disubstituted hydrazines and hydrogen phosphoryl compounds is accomplished. The reaction proceeds under mild conditions without the addition of any external oxidants and bases. This work reported here represents a direct P(O)–N–N bond formation with the advantages of being operationally simple, good functional group tolerance, and high atom and step economy. Furthermore, the selected compounds exhibit potential inhibitory activity against tumor cells, which can be used in the field of screening of anticancer agents as new chemical entities.

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Fe3O4@MgO nanoparticles as an efficient recyclable catalyst for the synthesis of phosphoroamidates via the Atherton–Todd reaction

Cited by 17 publications

References 59 publications

Opening up the Toolbox: Synthesis and Mechanisms of Phosphoramidates

Opening up the Toolbox: Synthesis and Mechanisms of Phosphoramidates

Synthesis, Molecular and Crystal Structures of Tetraethyl 1,3-Phenylenebis (Phosphoramidate) and Tetrapropyl 1,3-Phenylenebis (Phosphoramidate)

Copper-Catalyzed Phosphorylation of N,N-Disubstituted Hydrazines: Synthesis of Multisubstituted Phosphorylhydrazides as Potential Anticancer Agents

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