33650-14-5Relevant academic research and scientific papers
Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids
Ash, Jeffrey,Cordero, Paula,Huang, Hai,Kang, Jun Yong
, p. 6007 - 6014 (2021/07/21)
An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.
Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds
Handoko,Benslimane, Zacharia,Arora, Paramjit S.
supporting information, p. 5811 - 5816 (2020/07/27)
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.
Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate
Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
supporting information, p. 4938 - 4941 (2018/08/24)
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.
Alkyl Grignard cross-coupling of aryl phosphates catalyzed by new, highly active ionic iron(II) complexes containing a phosphine ligand and an imidazolium cation
Li, Zhuang,Liu, Ling,Sun, Hong-Mei,Shen, Qi,Zhang, Yong
, p. 17739 - 17747 (2016/11/18)
A novel family of ionic iron(ii) complexes of the general formula [HL][Fe(PR′3)X3] (HL = 1,3-bis(2,6-diisopropylphenyl)imidazolium cation, HIPr, R′ = Ph, X = Cl, 2; HL = HIPr, R′ = Cy, X = Cl, 3; HL = HIPr, R′ = Ph, X = Br, 4; HL = HIPr, R′ = Cy, X = Br, 5; HL = 1,3-bis(2,4,6-trimethylphenyl)imidazolium cation, HIMes, R′ = Cy, X = Br, 6) was easily prepared via a stepwise approach in 88%-92% yields. In addition, an ionic iron(ii) complex, [HIPr][Fe(C4H8O)Cl3] (1), has been isolated from the reaction of FeCl2(THF)1.5 with one equiv. of [HIPr]Cl in 90% yield and it can further react with one equiv. of PPh3 or PCy3, affording the corresponding target iron(ii) complex 2 or 3, respectively. All these complexes were characterized by elemental analysis, electrospray ionization mass spectrometry (ESI-MS), 1H NMR spectroscopy and X-ray crystallography. These air-insensitive complexes 2-6 showed high catalytic activities in the cross-coupling of aryl phosphates with primary and secondary alkyl Grignard reagents with a broad substrate scope, wherein [HIPr][Fe(PCy3)Br3] (5) was the most effective. Complex 5 also catalyzes the reductive cross-coupling of aryl phosphates with unactivated alkyl bromides in the presence of magnesium turnings and LiCl, as well as the corresponding one-pot acylation/cross-coupling sequence under mild conditions.
Triethylphosphate/phosphorus pentoxide as an efficient reagent for the phosphorylation of phenols
Kaboudin, Babak,Mostafalu, Ramin
experimental part, p. 776 - 780 (2012/06/30)
A simple, efficient, and novel method has been developed for the phosphorylation of phenols. Treatment of phenols with a mixture of triethylphosphate/phosphorus pentoxide gives the corresponding phosphate derivatives in good yields. This method is easy, rapid, and offers good yields for the phosphorylation of phenols. The reaction of triethylphosphate with phosphorus pentoxide was also studied by variable-temperature 31P-NMR spectroscopy. Copyright
Phosphorylation of phenols with diethyl chlorophosphonate on the surface of magnesia
Kaboudin
, p. 402 - 403 (2007/10/03)
Phosphorylation of phenols with diethyl chlorophosphonate on the surface of magnesia is an easy, rapid, safe and high-yielding reaction.
NICKEL-CATALYZED CROSS-COUPLING OF ARYL PHOSPHATES WITH GRIGNARD AND ORGANOALUMINIUM REAGENTS. SYNTHESIS OF ALKYL-, ALKENYL-, AND ARYLBENZENES FROM PHENOLS
Hayashi, Tamio,Katsuro, Yoshio,Okamoto, Yasuo,Kumada, Makoto
, p. 4449 - 4452 (2007/10/02)
Aryl phosphates derived from phenols were converted into alkyl-, alkenyl-, and aryl-benzenes in high yields by cross-coupling with various kinds of Grignard and organoaluminium reagents in the presence of nickel(II) catalysts.
