- Preparation of α-ketophosphonates by oxidation of α-hydroxyphosphonates with Pyridinium Chlorochromate (PCC)
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Various types of diethyl α-hydroxyphosphonates were converted efficiently to their corresponding diethyl α-ketophosphonates by pyridiinum chlorochromate (PCC) without cleavage of C(O) - P bond in the absence of solvent or in solution in high yields.
- Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara
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- Preparation of α-ketophosphonates by oxidation of α-hydroxyphosphonates with neutral alumina supported potassium permanganate (NASPP) under solvent-free conditions and potassium permanganate in dry benzene
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Various types of α-hydroxyphosphonates were converted to α-ketophosphonates in high yields by potassium permanganate in dry benzene or by neutral alumina supported potassium permanganate (NASPP) under solvent-free conditions.
- Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara
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- Surface-mediated solid-phase reactions: The preparation of acyl phosphonates by oxidation of 1-hydroxyphosphonates on the solid surface
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Alumina-supported CrO3, under solvent-free conditions, was found to be an efficient oxidizing reagent for the preparation of acyl phosphonates from 1-hydroxyphosphonates. This method is an easy, rapid, and high-yielding reaction for the prepara
- Kaboudin, Babak
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- A convenient and mild protocol for preparation of α – trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide
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A convenient and mild protocol was developed for the trimethylsilylation of α-hydroxyphosphonates using hexamethyldisilazane as the silylating agent in the presence of sulfamic acid (SA) as a heterogeneous solid acid catalyst in dichloromethane as the rea
- Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.
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- Enantioselective vinylogous aldol reaction of acylphosphonates with 3-alkylidene oxindoles
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A simple strategy for yielding chiral tertiary α-hydroxy phosphonates that integrates two highly biologically relevant scaffolds namely 3-alkylidene-2-oxindoles and phosphonates has been described. The hydrogen bonding ability of the bifunctional thiourea catalyst allows simultaneous dual activation of a vinylogous oxindole nucleophile and an acylphosphonate electrophile, affording hydroxyphosphonato-3-alkylidene-2-oxindoles as aldol adducts in high yields (up to 92%) with excellent stereocontrol (up to 99% ee).
- Jaiswal, Manish K.,Singh, Ravi P.,Singh, Sanjay
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supporting information
p. 7861 - 7866
(2021/09/28)
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- Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane
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Dess-Martin periodinane has been demonstrated for the first time to be an efficient reagent in metal - free oxidation of α-hydroxyphosphonates to α-ketophosphonates under ambient conditions. Acquiescent reaction conditions and a simple isolation procedure
- Kupwade, Ravindra V.,Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.
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- Visible photocatalysis of novel oxime phosphonates: Synthesis of β-aminophosphonates
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A novel type of oxime phosphonate was synthesized and used in the intermolecular cascade radical addition reaction of alkenes to access β-aminophosphonates via visible-light-driven N-centered iminyl radical-mediated and redox-neutral selective C-P single-bond cleavage in an active phosphorus radical route. The procedure is characterized by its ability to achieve the construction of Csp3-P and Csp3-N bonds without the requirement for oxidants and bases.
- Li, Yong-Hong,Wang, Chun-Hai,Gao, Su-Qian,Qi, Feng-Ming,Yang, Shang-Dong
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supporting information
p. 11888 - 11891
(2019/10/11)
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- Pd-catalyzed carbonylative access to aroyl phosphonates from (hetero)aryl bromides
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The first transition-metal catalysed carbonylation with a phosphorus nucleophile is presented. This transformation provides efficient and mild access to aroylphosphonates under mild conditions, thus ensuring a broad substrate scope. The utility of aroylph
- Lian, Zhong,Yin, Hongfei,Friis, Stig D.,Skrydstrup, Troels
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supporting information
p. 7831 - 7834
(2015/05/13)
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- Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst
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A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enanti
- Jang, Ki Po,Hutson, Gerri E.,Johnston, Ryne C.,McCusker, Elizabeth O.,Cheong, Paul H.-Y.,Scheidt, Karl A.
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supporting information
p. 76 - 79
(2014/01/23)
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- Nicotinium dichromate (= 3-carboxypyridinium dichromate; NDC) as an efficient reagent for the oxidative deamination of amines and aminophosphonates
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A new method for the efficient synthesis of aldehydes, ketones, and oxophosphonates from various types of amines (primary and secondary) and aminophosphonates via oxidative deamination by nicotinium dichromate (= 3-carboxypyridinium dichromate; NDC) is described.
- Sobhani, Sara,Aryanejad, Sima,Maleki, Mahdi Faal
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experimental part
p. 613 - 617
(2012/05/20)
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- Palladium-catalyzed asymmetric hydrogenation of N-hydroxya-imino phosphonates using bronsted acid as activator: The first catalytic enantioselective approach to chiral N-hydroxy-aamino phosphonates
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The enantioselective synthesis of ring-substituted [N-(hydroxy)amino] ACHTUNGTRENUNG(phenyl)methylphos- ACHTUNGTRENUNGphonic esters via asymmetric hydrogenation of the corresponding N-hydroxy-a-imino phosphonates with up to 90% ee was developed using cata
- Goulioukina, Nataliya S.,Shergold, Ilya A.,Bondarenko, Grigorii N.,Ilyin, Mikhail M.,Davankov, Vadim A.,Beletskaya, Irina P.
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supporting information
p. 2727 - 2733
(2013/01/15)
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- Rhodium-catalyzed enantioselective cyclizations of γ-alkynylaldehydes with acyl phosphonates: ligand- and substituent-controlled C-P or C-H bond cleavage
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It has been established that a cationic rhodium(I)/(R)-H8-BINAP or (R)-Segphos complex catalyzes two modes of enantioselective cyclizations of γ-alkynylaldehydes with acyl phosphonates via C-P or C-H bond cleavage. The ligands of the Rh(I) comp
- Masuda, Kengo,Sakiyama, Norifumi,Tanaka, Rie,Noguchi, Keiichi,Tanaka, Ken
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supporting information; experimental part
p. 6918 - 6921
(2011/06/21)
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- Oxidative deamination of α-aminophosphonates and amines by zinc dichromate trihydrate (ZnCr2O73H2O) under solvent-free conditions at room temperature
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A novel method for the rapid and efficient conversion of a variety of -aminophosphonates to α-ketophosphonates using ZnCr2O 73H2O via oxidative deamination under solvent-free conditions at room temperature is described. This method is also applicable to the rapid and highly selective oxidation of various types of ordinary amines (primary and secondary) to aldehydes and ketones in good to high yields. Georg Thieme Verlag Stuttgart New York.
- Sobhani, Sara,Maleki, Mahdi Faal
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experimental part
p. 383 - 386
(2010/04/05)
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- Preparation of α-ketophosphonates by oxidation of α-hydroxyphosphonates with chromium-based oxidants
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Various types of diethyl α-hydroxyphosphonates were efficiently converted to diethyl α-ketophosphonates by nicotinium dichromate (NDC), nicotinium chlorochromate (NCC), and isonicotinium dichromate (INDC) in high yields.
- Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara
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p. 1463 - 1471
(2007/10/03)
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- High yield preparation of α-ketophosphonates by oxidation of α-hydroxyphosphonates with zinc dichromate trihydrate (ZnCr2O7·3H2O) under solvent-free conditions
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Various types of α-hydroxyphosphonates were converted to α-ketophosphonates by zinc dichromate trihydrate in high yields and rates under solvent-free conditions.
- Firouzabadi, Habib,Iranpoor, Nasser,Sobhani, Sara,Sardarian, Ali-Reza
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p. 4369 - 4371
(2007/10/03)
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- A convenient and mild procedure for the preparation of α-keto phosphonates of 1-hydroxyphosphonates under solvent-free conditions using microwave
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The Reactions of 1-hydroxyphosphonates on the alumina-supported CrO3 are accelerated by microwave irradiation under solvent-free conditions to afford a high yielding synthesis of α-keto phosphonates.
- Kaboudin,Nazari
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p. 2245 - 2250
(2007/10/03)
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- The Schmidt reaction of dialkyl acylphosphonates
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The scope of the Schmidt rearrangement of ketones has been extended to dialkyl acylphosphonates (11a-11l). Surprisingly, it was found that 11a-11d and 11g, in which the acyl moiety was benzoyl alone or benzoyl bearing an electron-attracting or mildly electron-releasing substituent, yielded an overwhelming portion of products resulting from C-to-N migration of the aryl group (N-arylcarbamoylphosphonates, 12, and N-arylformamides, 15). Contrariwise, the arenecarbonylphosphonates, which carry a powerful electron-releasing p-alkoxy group, yielded products resulting from phosphonate group migration from C to N or elimination (dialkyl N-arenecarbonylphosphoramidates, 13, and arenecarbonitriles, 17, respectively). These counterintuitive results are rationalized by application of the concept of "degree of electron demand" to this area of intramolecular rearrangements. The possible existence of an additional pathway for the Schmidt rearrangement, involving protonation of the iminodiazonium ion, is proposed.
- Sprecher, Milon,Kost, Daniel
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p. 1016 - 1026
(2007/10/02)
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- Studies on organophosphorus compounds; LXXV: A facile synthesis of 1-(hydroxyamino)alkyl(or aryl)phosphonic acids
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Reduction of dialkyl 1-(hydroxyimino)alkyl(aryl)phosphonate 1 with borane-pyridine complex proceeds smoothly to give dialkyl 1-(hydroxyamino)alkyl(or aryl)phosphonate 2 which is then easily converted into the corresponding hydroxyaminophosphonic acid 3 by
- Yuan,Chen,Zhou,Maier
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p. 955 - 957
(2007/10/02)
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