- Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds
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We report a diaryldiselenide catalyst for cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds. The proposed organocatalytic cycle closely resembles the mechanism of the Atherton-Todd reaction, with the catalyst serving as a recyclable analogue of the halogenating agent employed in the named reaction. Phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.
- Handoko,Benslimane, Zacharia,Arora, Paramjit S.
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supporting information
p. 5811 - 5816
(2020/07/27)
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- Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate
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A metal-, toxic chloride reagent-free activating strategy of various phosphates has been developed. This method enables the facile synthesis of functional phosphates such as alkyl phosphates, aza phosphates, thiophosphate, and mixed diaryl phosphates. A transient phosphorylpyridin-1-ium species in situ generated from phosphates with Tf2O/pyridine readily undergoes a substitution reaction with diverse nucleophiles to form versatile phosphate compounds.
- Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
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supporting information
p. 4938 - 4941
(2018/08/24)
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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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- New benzotriazole-based reagents for the phosphonylation of various N-, O-, and S-nucleophiles
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Benzotriazole surrogates showing higher stabilities than the corresponding chlorophosphates, allow phosphonylation of a variety of N-, O-, and S-nucleophiles in good yields.
- Panmand, Deepak S.,Tiwari, Anand D.,Panda, Siva S.,Monbaliu, Jean-Christophe M.,Beagle, Lucas K.,Asiri, Abdullah M.,Stevens, Christian V.,Steel, Peter J.,Hall, C. Dennis,Katritzky, Alan R.
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supporting information
p. 5898 - 5901
(2015/01/08)
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- Stereospecific aerobic oxidative dehydrocoupling of P(O)H bonds with amines catalyzed by copper
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Copper-catalyzed stereospecific oxidative dehydrocouplings of P(O)H bonds with amines under air took place effi-ciently at room temperature to afford the corresponding amidophosphorus compounds in high yields. Mechanistic studies showed that this dehydroc
- Zhou, Yongbo,Yang, Jia,Chen, Tieqiao,Yin, Shuang-Feng,Han, Daoqing,Han, Li-Biao
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supporting information
p. 400 - 402
(2014/04/17)
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- Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonates
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The copper-catalysed oxidative coupling of amines and H-phosphonates to produce phosphoramidates has been achieved using CuI as the catalyst and O 2 (present in air) as the sole oxidant.
- Fraser, Jamie,Wilson, Laura J.,Blundell, Rebecca K.,Hayes, Christopher J.
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supporting information
p. 8919 - 8921
(2013/09/24)
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- Trichlorocyanuric acid: An efficient reagent for one-pot synthesis of Ptychodiscus brevis (PB-1) toxin and its derivatives
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Trichlorocyanuric acid is an efficient regent for simple and one-pot synthesis of dialkyl, N-cycloctylphosphoraamidates (PB-1) and its various derivatives in excellent yields. The procedure is operationally simple and involves the reaction of various dialkylphosphites with trichloroisocyanuric acid in acetonitrile and subsequent treatment with amines in presence KF-celite to give PB-1 and derivatives.
- Gupta, Arvind K.,Acharya, Jyotiranjan,Dubey, Devendra K.,Kaushik, Mahabir P.
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- New route to O,O-diethyl phosphorocyanidate
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A new and efficient route for synthesis of O, O-Diethyl Phosphorocyanidate by decomposition of diethyl phosphoryl-1,2,4,-dithiazolin-5-one was discussed. The use of phosphorocyanidates as coupling reagents in peptide chemistry and other applications of these compounds in organic synthesis was also demonstrated. It was found that these compounds were relatively unstable and could decompose easily, especially in the presence of water with the formation of hydrogen cyanide. A new efficient route to O, O-dialkyl phosphorocyamidates was offered, which were not contaminated by isomeric isocyanidates and could be used as the substrates for further synthetic purposes.
- Lopusinski, Andrzej
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p. 395 - 397
(2007/10/03)
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- Carbodiimide compounds, polymers containing same and coating compositions containing said polymers
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Carbodiimide compounds having the following structural formula are claimed: STR1 Z being selected from the group consisting of the following moieties: STR2 wherein R1 represents an alkylidene radical; R2 represents hydrogen or an alk
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- A Simple Test for Diffusion-Limited Reactions. Near-Diffusion-Controlled Nitrene Insertion into C-H Bonds
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A test for diffusion-controlled reactions is described.It is based on a simple experiment, wherein a reactive intermediate competes for two reagents containing a different number of reactive sites.This approach allows one to estimate rate constants of rapid reactions (i.e., kr ca. kd without absolute rate measurements.The test is applied to reaction of (diethoxyphosphoryl)nitrene with hydrocarbons in perfluorinated solvents.The photogenerated singlet nitrene undergoes efficient insertion into C-H bonds, and its reactivity is unaffected by the presence of oxygen.The insertion of the nitrene into a tertiary C-H bond is found to be near-diffusion-controlled with kobs ca. 0.3kdif = 3 * 1E9 M-1 s-1.Increased selectivity for insertion into tertiary versus primary C-H bonds is observed in perfluorohexane (9.7) as compared to a hydrocarbon solvent (5.7).This diminished reactivity of the nitrene is considered as evidence for complex formation between the singlet nitrene and a solvent molecule.The rate of the complexed-singlet to triplet intersystem crossing is estimated to be 8 * 1E8 s-1.The triplet nitrene reacts by hydrogen abstraction and is scavenged by oxygen.
- Maslak, Przemyslaw
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p. 8201 - 8207
(2007/10/02)
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- Direct Conversion of Diethyl Hydrogen Phosphate into Diethyl Phosphoramides
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The effective, one-step transformation of diethyl hydrogen phosphate into diethyl phosphoramides by using hexamethyltriaminodibromophosphorane prepared "in situ" is described. - Keywords: Hexamethyltriaminodibromophosphorane; Intermolecular dehydration
- Zwierzak, Andrzej,Osowska-Pacewicka, Krystyna
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p. 117 - 120
(2007/10/02)
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- REACTION OF SULFENAMIDES WITH DI-ALKYL AND TRIALKYL PHOSPHITES. AN EFFICIENT SYNTHESIS OF PHOSPHORAMIDATES BY UNUSUAL SUBSTITUTION AT S-N BOND IN (2-BENZOTHIAZOLYL)SULFENAMIDES
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Regioselective attack of the trivalent phosphorus atom of dialkyl and trialkyl phosphites on either nitrogen or sulfur atom of sulfenamides has been found.The reaction of phenylsulfenamides with dialkyl phosphites yielded phosphorothiolates, whereas the treatment of (2-benzothiazolyl)sulfenamides with dialkyl and trialkyl phosphites gave phosphoramidates in excellent yields.
- Torii, Sigeru,Sayo, Noboru,Tanaka, Hideo
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p. 695 - 698
(2007/10/02)
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