- A (E) - 2-aryl ethylene cinnamenyl method for preparing ester derivative
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The invention discloses method for preparing (E)-2-aryl vinyl phosphonate derivatives. The method comprises the specific following steps of dissolving 1-nitro-2-aryl-vinyl derivatives, a phosphorus reagent, an accelerator manganese acetate and a catalyst copper acetate in a solvent and reacting at 20-100 DEG C to obtain the (E)-2-aryl vinyl phosphonate derivatives. According to the method disclosed by the invention, the 1-nitro-2-aryl-vinyl derivatives are adopted as starting materials, the raw materials are easily available and have multiple varieties; the products obtained by the method disclosed by the invention are multiple and can be directly applied and can be also used for other further reaction; according to the method, the use of precious metal reagents and other additives is avoided; and meanwhile, the synthetic route is short, reaction conditions are mild, the reaction operation and post-treatment process are simple, the yield is high and the method is suitable for scale production.
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Paragraph 0091-0093
(2017/03/08)
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- Manganese(iii)-mediated alkenyl Csp2-P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites
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Mn(OAc)3-mediated tandem phosphonyl radical addition to β-nitrostyrenes followed by denitration to form (E)-2-alkenyl phosphonates in good yield is described.
- Xue, Jian-Fei,Zhou, Shao-Fang,Liu, Ye-Ye,Pan, Xiangqiang,Zou, Jian-Ping,Asekun, Olayinka Taiwo
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p. 4896 - 4902
(2015/05/05)
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- Synthesis of diethyl 2-(aryl)vinylphosphonate by the Heck reaction catalysed by supported palladium catalysts
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The synthesis of diethyl 2-(aryl)vinylphosphonate through direct Heck coupling reaction of the diethyl vinylphosphonate with aryl or heteroaryl halides catalysed by solid materials ([Pd(NH3)4]/NaY, Pd/C, PdO/SiO2) is reported. After optimising the reaction conditions (1.3 mol% [Pd(NH3)4]/NaY, DMF, K2CO 3, 110-140 °C), various aryl and heteroaryl halides were engaged in this reaction leading in all cases good to high yields. Interestingly, when using activated aryl bromides the palladium loading could be lowered to only 0.25 mol%. While highly active when coupling aryl iodides (i.e. only 0.15 mol% required), the PdO/SiO2 catalyst was found to be inactive when considering aryl bromides. Deep study of this catalytic material revealed that in the case of aryl bromides, absence of in situ reduction of the catalyst precursor prevents the cross-coupling reaction with this latter material.
- Tarabay, Jinane,Al-Maksoud, Walid,Jaber, Farouk,Pinel, Catherine,Prakash, Swamy,Djakovitch, Laurent
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experimental part
p. 124 - 133
(2011/02/23)
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- Synthesis of diethyl 2-(aryl)vinylphosphonates by the Heck reaction catalysed by well-defined palladium complexes
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Pd-catalysed procedures for the direct Heck arylation of diethyl vinylphosphonate with various aryl or heteroaryl halides toward the synthesis of diethyl 2-(aryl)vinylphosphonates are reported. Several homogeneous catalytic systems (i.e. Herrmann palladacycle, Nolan (NHC)-palladium catalyst, Pd(OAc)2/PPh3) were used and compared within the study. High conversions and selectivities were achieved under optimised conditions (2 mol% [Pd], NMP, K2CO3, 140 °C) whatever the homogeneous catalyst used.
- Al-Maksoud, Walid,Mesnager, Julien,Jaber, Farouk,Pinel, Catherine,Djakovitch, Laurent
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experimental part
p. 3222 - 3231
(2010/01/11)
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- Reaction of diethyl thiocyanatomethylphosphonate with aldehydes as a route to diethyl Z-1-alkenylphosphonates
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Diastereoselective synthesis of diethyl Z-1-alkenylphosphonates from easily available diethyl thiocyanatomethylphosphonate and aromatic aldehydes has been developed. Olefination of the aldehydes occurs under mild conditions and affords the title compounds with moderate yields. A plausible mechanism of the above-mentioned reaction is also discussed.
- Blaszczyk, Roman,Gajda, Tadeusz
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p. 732 - 739
(2008/03/18)
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- Knoevenagel reaction of diethylphosphonoacetic acid: A facile route to diethyl (E)-2-arylvinylphosphonates
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Knoevenagel reaction of aromatic aldehydes or α-substituted aliphatic aldehydes with diethylphosphonoacetic acid leads to the formation of 3-substituted-2-(diethoxyphosphoryl)acrylic acids. Decarboxylation of the resulting (E)-3-aryl-2-(diethoxyphosphoryl)acrylic acids afforded diethyl (E)-2-arylvinylphosphonates. Direct synthesis of diethyl vinylphosphonates from some aromatic aldehydes and formaldehyde is also reported. Georg Thieme Verlag Stuttgart.
- Krawczyk, Henryk,Albrecht, Lukasz
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p. 2887 - 2896
(2007/10/03)
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- Palladium-Catalyzed Arylation of Vinyl- and α-Substituted Vinylphosphonates
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Arylation of vinyl- and α-substituted vinylphosphonates by various arylating agents, in particular, aryl iodides and aroyl chlorides, in aqueous-organic media, catalyzed by "ligand-free" palladium, is a simple route to E-β-arylvinylphosphonates.
- Demik, N. N.,Kabachnik, M. M.,Novikova, Z. S.,Beletskaya, I. P.
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