60585-76-4

Upstream product

• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 682-30-4 Diethyl vinylphosphonate 
• 589-87-7 1,4-bromoiodobenzene 
• 3156-37-4 4-bromo-β-nitrostyrene 
• 762-04-9 phosphonic acid diethyl ester 
• 3156-37-4 (E)-1-bromo-4-(2-nitrovinyl)benzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 3095-95-2 diethylphosphonoacetic acid 
• 873061-60-0 (E)-2-diethoxyphosphoryl-3-(4-bromophenyl)acrylic acid 
• 1660-94-2 Tetraethyl methylenediphosphonate 

Downstream Products

• 97006-84-3 [2-(4-Bromo-phenyl)-1,2-dihydroxy-ethyl]-phosphonic acid diethyl ester 
• 3343-45-1 4-bromo-2-hydroxyacetophenone 

Relevant academic research and scientific papers

Cu(i)/Fe(III)-Catalyzed C-P cross-coupling of styrenes with H-phosphine oxides: A facile and selective synthesis of alkenylphosphine oxides and β-ketophosphonates

Cu(i)/Fe(iii)-Catalyzed phosphorylation and oxyphosphorylation of styrenes with H-phosphonates which can be controlled by varying the reaction temperature are developed. This study offers a new and expedient strategy for the synthesis of useful alkenylphosphine oxides and β-ketophosphonates in satisfactory yields. Moreover, the transformation is proposed to proceed via a radical process and exhibits a broad substrate scope and good functional group tolerance.

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.

Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts

The invention pertains to the use of Group 8 transition metal carbene complexes as catalysts for olefin cross-metathesis reactions. In particular, ruthenium and osmium alkylidene complexes substituted with an N-heterocyclic carbene ligand are used to catalyze cross-metathesis reactions to provide a variety of substituted and functionalized olefins, including phosphonate-substituted olefins, directly halogenated olefins, 1,1,2-trisubstituted olefins, and quaternary allylic olefins. The invention further provides a method for creating functional diversity using the aforementioned complexes to catalyze cross-metathesis reactions of a first olefinic reactant, which may or may not be substituted with a functional group, with each of a plurality of different olefinic reactants, which may or may not be substituted with functional groups, to give a plurality of structurally distinct olefinic products. The methodology of the invention is also useful in facilitating the stereoselective synthesis of 1,2-disubstituted olefins in the cis configuration.

Stereoselective synthesis of vinylphosphonates and phosphine oxides via silver-catalyzed phosphorylation of styrenes

An efficient and stereoselective synthesis of vinylphosphonates and phosphine oxides was developed starting from styrenes using AgNO3 as the catalyst and K2S2O8 as the oxidant. The success of the reaction was fo

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.

Knoevenagel reaction of diethylphosphonoacetic acid: A facile route to diethyl (E)-2-arylvinylphosphonates

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.

Synthesis of vinyl- and allylphosphonates by olefin cross-metathesis

Substituted allyl and vinyl phosphonates have been prepared for the first time via intermolecular olefin cross-metathesis (CM) using 1,3-dimesityl-4,5-dihydro-imidazol-2-ylidene ruthenium alkylidene complex 3 in good yield. A variety of terminal olefins, styrenes, and geminally disubstituted olefins have been successfully employed in these reactions. In addition, CM of vinylphosphonates provide exclusive E olefin stereochemistry.