16703-95-0Relevant academic research and scientific papers
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
Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.
, (2021/10/05)
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
Enantioselective vinylogous aldol reaction of acylphosphonates with 3-alkylidene oxindoles
Jaiswal, Manish K.,Singh, Ravi P.,Singh, Sanjay
supporting information, p. 7861 - 7866 (2021/09/28)
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).
Diazophosphonates: Effective Surrogates for Diazoalkanes in Pyrazole Synthesis
Green, Michael T.,Hayes, Christopher J.,Inman, Martyn,Lewis, William,Moody, Christopher J.,Nicolle, Simon M.,Ruffell, Katie,Smith, Frances R.
supporting information, p. 13703 - 13708 (2021/09/09)
Diazophosphonates, readily prepared from α-ketophosphonates by oxidation of the corresponding hydrazones in batch or in flow, are useful partners in 1,3-dipolar cycloaddition reactions to alkynes to give N-H pyrazoles, including the first intramolecular examples of such a process. The phosphoryl group imbues a number of desirable properties into the diazo 1,3-dipole. The electron-withdrawing nature of the phosphoryl stabilizes the diazo compound making it easier to handle, whilst the ability of the phosphoryl group to migrate readily in a [1,5]-sigmatropic rearrangement enables its transfer from C to N to aromatize the initial cycloadduct, and hence its facile removal from the final pyrazole product. Overall, the diazophosphonate acts as a surrogate for the much less stable diazoalkane in cycloadditions, with the phosphoryl group playing a vital, but traceless, role. The cycloaddition proceeds more readily with alkynes bearing electron-withdrawing groups, and is regiospecific with asymmetrical alkynes. The potential of diazophosphonates for use in bioorthogonal cycloadditions is demonstrated by their facile addition to strained alkynes.
Visible photocatalysis of novel oxime phosphonates: Synthesis of β-aminophosphonates
Li, Yong-Hong,Wang, Chun-Hai,Gao, Su-Qian,Qi, Feng-Ming,Yang, Shang-Dong
supporting information, p. 11888 - 11891 (2019/10/11)
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.
Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates
Kayal, Satavisha,Mukherjee, Santanu
supporting information, p. 5508 - 5511 (2015/11/18)
A cascade aldol-cyclization reaction between 3-isothiocyanato oxindoles and α-ketophosphonates has been developed for the synthesis of β-amino-α-hydroxyphosphonate derivatives. Catalyzed by a quinine-based tertiary amino-thiourea derivative, this reaction
Pd-catalyzed carbonylative access to aroyl phosphonates from (hetero)aryl bromides
Lian, Zhong,Yin, Hongfei,Friis, Stig D.,Skrydstrup, Troels
supporting information, p. 7831 - 7834 (2015/05/13)
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
Synthesis of acylphosphonates by a palladium-catalyzed phosphonocarbonylation reaction of aryl iodides with phosphites
Masuda, Yusuke,Ishida, Naoki,Murakami, Masahiro
supporting information, p. 321 - 324 (2015/02/05)
Acylphosphonates are conveniently synthesized from aryl iodides by a palladium-catalyzed reaction with dialkyl phosphites under an atmospheric pressure of carbon monoxide. The reaction demonstrates the first example of the use of phosphorus nucleophiles in related metal-catalyzed carbonylation reactions.
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
Goulioukina, Nataliya S.,Shergold, Ilya A.,Bondarenko, Grigorii N.,Ilyin, Mikhail M.,Davankov, Vadim A.,Beletskaya, Irina P.
supporting information, p. 2727 - 2733 (2013/01/15)
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
Nicotinium dichromate (= 3-carboxypyridinium dichromate; NDC) as an efficient reagent for the oxidative deamination of amines and aminophosphonates
Sobhani, Sara,Aryanejad, Sima,Maleki, Mahdi Faal
experimental part, p. 613 - 617 (2012/05/20)
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.
