- Aryltrimethylammonium Tetrafluoroborates in Nickel-Catalyzed C–P Bond-Forming Reactions
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Abstract: The first nickel-catalyzed phosphorylation of aryltrimethylammonium tetrafluoroborates with the formation of C–P bond instead of C–N has been developed. Starting from easily available and inexpensive aromatic amines, a variety of important arylphosphonates have been synthesized in moderate to excellent yields.
- Li, Chun Jing
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p. 954 - 960
(2021/07/22)
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- BICYCLIC HETEROARYL DERIVATIVES AS ECTONUCLEOTIDE PYROPHOSPHATASE PHOSPHODIESTERASE 1 INHIBITORS
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The present disclosure provides certain bicyclic heteroaryl compounds that inhibit ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1) enzymatic activity and are therefore useful for the treatment of diseases and conditions modulated at least in part by ENPP1. In some embodiments, the bicyclic heteroaryl compounds includes those of Formula (I). Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.
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Paragraph 0545
(2020/10/21)
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- Nickel-Catalyzed Phosphorylation of Phenol Derivatives via C-O/P-H Cross-Coupling
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An efficient nickel-catalyzed phosphorylation of phenol derivatives with P(O)-H compounds via C-O/P-H cross-coupling is described. Under the reaction conditions, various phenyl pivalates coupled readily with hydrogen phosphoryl compounds to afford the corresponding coupling products aryl phosphonates and aryl phosphine oxides in good to high yields.
- Yang, Jia,Xiao, Jing,Chen, Tieqiao,Han, Li-Biao
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p. 3911 - 3916
(2016/05/24)
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- Palladium-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with H-phosphonate diesters
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A novel and convenient palladium-catalyzed cross-coupling reaction of H-phosphonate diesters with sodium arylsulfinates was developed via desulfitation in the presence of silver carbonate and tetra-butylammonium chloride. This method is highly efficient and provides a rapid access to a broad spectrum of arylphosphonate diesters in good to excellent yields.
- Miao, Tao,Wang, Lei
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supporting information
p. 967 - 971
(2014/04/03)
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- Palladium-catalyzed desulfitative C-P coupling of arylsulfinate metal salts and H-phosphonates
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Catalyzed by palladium(ii) chloride, a diverse range of arylsulfinate sodium, potassium, lithium, silver, zinc, and copper salts undergo desulfination/C-P coupling with H-phosphonates, in the presence of silver(i) carbonate as oxidant, to produce useful arylphosphonates under microwave irradiation. the Partner Organisations 2014.
- Li, Junchen,Bi, Xiaojing,Wang, Hongmei,Xiao, Junhua
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p. 19214 - 19217
(2014/05/20)
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- Synthesis of aryl and arylmethyl phosphonates by cross-coupling of aryl or arylmethyl halides (X = I, Br and Cl) with diisopropyl H-phosphonate
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An efficient and generally applicable protocol for the palladacycle- catalysed arylation or K2CO3-promoted arylmethylation of diisopropyl H-phosphonate has been developed. The remarkable features of the palladacycle-catalysed arylation reaction include wide substrate scope (aryl iodides, bromides and chlorides), significant shortening of the reaction time (2 or 3 h) and a low catalyst loading of 1 mol-%. Note that with the base K 2CO3 as promoter, arylmethylation could be achieved without any palladium catalyst. Moreover, the first example of a palladium-catalysed phosphonation of inactive electron-rich aryl chlorides with tBuOK as the base has been realized. This result could be considered an important improvement and complement to earlier work of Montchamp and Han, whose catalytic systems are typically compatible with electron-deficient and electron-neutral aryl chlorides.
- Xu, Kai,Hu, Hao,Yang, Fan,Wu, Yangjie
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supporting information
p. 319 - 325
(2013/02/25)
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- Palladacycle-catalyzed phosphonation of aryl halides in neat water
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An efficient and generally applicable protocol for the palladacycle- catalyzed arylation of diisopropyl H-phosphonate in water was developed. The remarkable features of this C-P bond-forming reaction include wide substrate scope including the inactive electron-rich and electron-neutral aryl chlorides, the weak inorganic base KF instead of strong bases such as KOtBu or NaOtBu for the activation of C-Cl bond, and the addition of isopropanol to avoid the decomposition of diisopropyl H-phosphonate.
- Xu, Kai,Yang, Fan,Zhang, Guodong,Wu, Yangjie
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supporting information
p. 1055 - 1060
(2013/07/26)
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- A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester
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A new and readily available bidentate ligand, namely, pyrrolidine-2- phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.
- Rao, Honghua,Jin, Ying,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 3636 - 3646
(2008/02/03)
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- Hypervalent iodine in synthesis. 52. Palladium-catalyzed arylation of O,O-dialkyl phosphites with diaryliodonium salts: A convenient method for synthesis of arylphosphonates
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Palladium-catalyzed coupling reaction of diaryliodonium salts with O,O-dialkyl phosphites gave arylphosphonates in good yields.
- Zhou,Chen
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p. 3289 - 3294
(2007/10/03)
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- Palladium-Catalyzed Phase-Transfer Arylation of Dialkyl Phosphonates
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Palladium-catalyzed phase-transfer arylation of dialkyl phosphonates with various iodo- and bromoarenes has been studied. The arylation has also been effected in the absence of ligand. A simple preparative procedure for synthesizing arylphosphonic acids has been developed.
- Kabachnik,Solntseva,Izmer,Novikova,Beletskaya
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- THE KINETICS AND MECHANISM OF THE REACTION OF TRICO-ORDINATE PHOSPHORUS COMPOUNDS WITH TETRACYANOQUINODIMETHANE AND TETRACYANOETHYLENE
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Trico-ordinate phosphorus compounds, ArnP(OPri)3-n where n = 0-3, react with tetracyanoquinodimethane (TCNQ) in acetonitrile in the presence of water to give the corresponding phosphoryl compounds, ArnP(O)(OPri)3-n and 1,4-bis-dicyanomethylbenzene (TCNQH2) in quantitative yield.The kinetics of these reactions are reported together with the Hammett ρ-parameters from variation of substituents in the aryl group for n = 1,2 and 3.On the basis of the available evidence, a mechanism is proposed involving one electron transfer from phosphorus (the donor) to TCNQ.A kinetic study of the reaction of triarylphosphines with TCNE in aqueous acetonitrile, however, suggests rate-limiting nucleophilic attack on nitrogen rather than the radical cation mechanism.Key words: Tricoordinate phosphorus, tetracyanoquinodimethane, tetracyanoethylene, kinetics, mechanism.
- Hall, C. D.,Beer, P. D.,Powell, R. L.,Naan, M. P.
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p. 145 - 156
(2007/10/02)
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- The Kinetics and Mechanism of the Reaction of Tricoordinate Phosphorus Compounds with Diaryl Trisulfides
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Kinetic data and activation parameters are reported for the reaction of a series of tricoordinate phosphorus compounds, , with diaryl trisulfides.The second-order rate coefficients for series of arylphosphines, phosphinites and phosphonites, correlate with the Hammett ? constants of the aryl substituents with ρ values of -1.1, -1.1 and -1.1 respectively and these results are discussed in terms of a biphilic mechanism analogous to that proposed for the reaction of tricoordinate phosphorus with S8.
- Hall, C. Dennis,Tweedy, Bruce R.,Kayhanian, Robert,Lloyd, John R.
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p. 775 - 779
(2007/10/02)
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