- Efficient synthesis of α-substituted ethylphosphonates via CuH-catalyzed conjugate reduction of terminal alkenylphosphonate
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An unprecedented approach toward synthesis of α-substituted ethylphosphonates based on CuH-catalyzed conjugate reduction of vinylphosphonates has been successfully developed. This protocol features mild conditions, broad substrate scope, good functional group compatibility, high overall efficiencies, and easy gram-scale synthesis. The Cu-catalyzed reduction takes place in a highly selective manner on the phosphono substituted C[dbnd]C bond in the case of the reaction of alkenylphosphonates bearing both phosphono and alkyl or aryl substituted alkene moieties. Furthermore, the result of competitive reaction indicates that the Cu-catalyzed conjugate reduction of vinylphosphonate is more challenging and reproducible than the corresponding acrylate's reaction.
- Zhang, Li,Fang, Yewen,Jin, Xiaoping,Guo, Ting,Li, Ruifeng,Li, Yan,Li, Xie,Yang, Yi,Yuan, Meijuan,Tian, Zongming
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supporting information
p. 4538 - 4541
(2017/11/03)
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- Method for synthesizing alpha-aryl ethyl phosphonate
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The invention discloses a method for synthesizing alpha-aryl ethyl phosphonate.The method comprises the following steps that alpha-aryl vinyl phosphonate, potassium phosphate and o-nitro-benzenesulfonyl hydrazide are added into a reactor; after vacuumizing is conducted, N2 is introduced to remove oxygen; under the protection of N2, anhydrous acetonitrile is added, and stirring is conducted for 5-10 h at room temperature; after the reaction is finished, water is added into a reaction mixture for dilution, extraction is conducted with ethyl acetate, drying is conducted with sodium sulphate anhydrous, mixed liquor of petroleum ether and ethyl acetate serves as eluent, column chromatography isolation is conducted, distillation is conducted finally, and alpha-aryl ethyl phosphonate is obtained.According to the method for synthesizing alpha-aryl ethyl phosphonate, transition metal does not participate, the substrate universality is good, the compatibility of a functional group is high, the reaction condition is mild, the reaction efficiency is high, and operation is safe, easy and convenient.
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Paragraph 0028; 0029; 0030
(2016/11/24)
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- Metal-free diimide reduction of alkenylphosphonates: simple and efficient protocol for the synthesis of α-substituted ethylphosphonates
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A simple and straightforward method for the synthesis of α-substituted ethylphosphonates via diimide reduction strategy is described. With K3PO4 or Na2CO3 as the basic additive, a range of terminal alkenylphosph
- Fang, Yewen,Yuan, Meijuan,Jin, Xiaoping,Zhang, Li,Li, Ruifeng,Yang, Shaoshuai,Fang, Mei
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supporting information
p. 1368 - 1371
(2018/03/23)
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- Palladium-catalyzed hydrophosphonylation of alkenes with dialkyl H-phosphonates
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The palladium-catalyzed hydrophosphonylation of alkenes with previously unreactive acyclic dialkyl H-phosphonates has been developed. A catalyst system based on palladium/DavePhos or palladium/SPhos enables the transformation of various alkenes to phospho
- Candy, Mathieu,Rousseaux, Sophie A. L.,Sanroman, Alberto Cirugeda,Szymczyk, Monika,Kafarski, Pawel,Leclerc, Eric,Vrancken, Emmanuel,Campagne, Jean-Marc
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supporting information
p. 2703 - 2708
(2014/09/29)
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- Palladium(II)-catalyzed ortho-arylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates
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The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed ortho-arylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-ary
- Meng, Xiangjian,Kim, Sunggak
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p. 11247 - 11254
(2013/12/04)
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- Promotion of Dehydrazination by Nitrobenzensulfonyl Group from Phosphorus-hydrazone Adducts
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Dehydrazination of adducts of phenylsulfonylhydrazones and phosphorus compounds was promoted by a nitro substituent on the ring to afford derivatives of a phosphine oxide and phosphonates.
- Yamashita, Mitsuji,Takeuchi, Jun,Nakatani, Kaname,Oshikawa, Tatsuo,Inokawa, Saburo
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p. 377 - 378
(2007/10/02)
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