93032-47-4

Upstream product

• 22568-07-6 1-chloro-2-(2-nitrovinyl)benzene 
• 762-04-9 phosphonic acid diethyl ester 
• 22568-07-6 1-chloro-2-[(E)-2-nitrovinyl]benzene 
• 694-80-4 2-bromo-1-chlorobenzene 
• 682-30-4 Diethyl vinylphosphonate 
• 41849-03-0 diethoxyphosphorylmethyl-lithium 
• 683-08-9 Diethyl methylphosphonate 
• 1660-94-2 Tetraethyl methylenediphosphonate 
• 89-98-5 2-chloro-benzaldehyde 

Relevant academic research and scientific papers

A (E) - 2-aryl ethylene cinnamenyl method for preparing ester derivative

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.

Silver-catalyzed synthesis of 2-arylvinylphosphonates by cross-coupling of β-nitrostyrenes with: H -phosphites

An efficient protocol for stereoselective synthesis of 2-arylvinylphosphonates has been developed via AgNO3-catalyzed cross-coupling of β-nitrostyrenes with dialkyl H-phosphites under mild conditions. By losing the nitro group of β-nitrostyrene

Manganese(iii)-mediated alkenyl Csp2-P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites

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.

Synthesis of diethyl 2-(aryl)vinylphosphonate by the Heck reaction catalysed by supported palladium catalysts

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.

Synthesis of diethyl 2-(aryl)vinylphosphonates by the Heck reaction catalysed by well-defined palladium complexes

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.

A convenient (E)-stereoselective synthesis of alkenylphosphonates

Diethyl (E)-alkenylphosphonates have been prepared stereoselectively by dehydration of the corresponding β-hydroxyphosphonates using DCC/CuCl2 in refluxing toluene. Starting β-hydroxyphosphonates were obtained in high yield from diethyl methylphosphonate.