113569-00-9

Upstream product

• 140-10-3 (E)-3-phenylacrylic acid 
• 500555-16-8 (2,3-dibromo-3-phenyl-propylidene)-malonic acid dimethyl ester 
• 621-82-9 Cinnamic acid 
• 67-66-3 chloroform 
• 10035-10-6 hydrogen bromide 
• 79-15-2 N-bromoacetamide 
• 756769-71-8 3-phenyl-3-sulfopropanoic acid 
• 7789-69-7 phosphorus pentabromide 
• 140-10-3 cis-cinnamic acid 
• 100-52-7 benzaldehyde 
• 64-17-5 ethanol 
• 6286-30-2 2,3-dibromo-3-phenylpropanoic acid 
• 71-43-2 benzene 
• 34882-18-3 2-bromo-3-hydroxy-3-phenyl-propanoic acid 

Downstream Products

• 103-64-0 bromostyrene 
• 588-73-8 (Z)-β-bromostyrene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 121-39-1 (2RS,3RS)-2,3-epoxy-3-phenyl-propionic acid ethyl ester 
• 121-39-1 ethyl 3-phenylglycidate 
• 53663-24-4 2,3,3-triphenyl-propionic acid 
• 124-38-9 carbon dioxide 
• 34882-18-3 2-bromo-3-hydroxy-3-phenyl-propanoic acid 
• 122-78-1 phenylacetaldehyde 
• 621-82-9 Cinnamic acid 
• 637-44-5 phenylpropyolic acid 
• 15813-24-8 (Z)-2-bromo-3-phenylacrylic acid 
• 704-77-8 (E)-3-Bromo-3-phenyl-acrylic acid 
• 936-44-7 3-phenylpyrrolidine 

Relevant academic research and scientific papers

Convenient and stereoselective synthesis of (Z)-1-bromo-1-alkenes by microwave-induced reaction

(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time (0.2-1.0 min) by microwave irradiation of the corresponding 2,3-dibromoalkanoic acids in DMF in the presence of triethylamine.

cis-bromination of encapsulated alkenes

Inside changes! In striking contrast to the trans-bromination of the free acid, bromination of the bridging cinnamato ligand in 1 proceeds highly diastereoselectively to give the syn-brominated complex 2. A possible explanation for this is that the bromination of 1 proceeds within a confined environment. Since the brominated products can be liberated from the binding pocket of the dinuclear complexes, the metal complexes can be used as reagents for the cis-bromination of olefins with anchoring RCO2- functions.

Catalyst-Free 1,2-Dibromination of Alkenes Using 1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) as a Bromine Source

A direct 1,2-dibromination method of alkenes is realized using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as a bromine source. This reaction proceeds under mild reaction conditions without the use of a catalyst and an external oxidant. Various sorts of alkene substrates are transformed into the corresponding 1,2-dibrominated products in good to excellent yields with broad substrate scope and exclusive diastereoselectivity. This method offers a green and practical approach to synthesize vicinal dibromide compounds.

A Facile Access to trans -3-Styryl-4-hydrazinocyclopentenes via Palladium-Catalyzed Ring Opening of Diazanorbornenes with (Z)-β-Bromostyrenes/2,3-Dibromohydrocinnamic Acids

trans -3-Styryl-4-hydrazinocyclopentenes have been synthesized via palladium-catalyzed desymmetrization of diazanorbornenes with (Z)-β-bromostyrenes. The reaction also works well with (Z)-β-bromostyrenes generated in situ from 2,3-dibromohydrocinnamic acids. The synthesized hydrazinocyclopentenes provide an easy route towards synthetic intermediates of many scaffolds of biological potential.

Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization

An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.

Chloro/bromotrimethylsilane-Cu(NO3)2·3H2O: Safe and efficient reagent system for the decarboxylative ipso-nitration and dibromination of cinnamic acids

Further synthetic potential of halotrimethylsilane-nitrate salt mixture is revealed. A mixture of TMSX-Cu(NO3)2·3H2O system is found to be an efficient reagent system for both the decarboxylative nitration (ipso-nitration) when X?=?Cl, and dibromination of cinnamic acids, with X?=?Br, under mild conditions. The reactions are safe and simple, affording the corresponding products (E)-β-nitrostyrenes, and anti-2,3-dibromo-3-phenylpropanoic acids in high yields with high selectivity in a relatively short time. Use of hazardous and toxic nitrating systems such as acetyl nitrate and brominating agents such as molecular bromine can be avoided.

Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates

Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh3)4 or Pd(PPh3)2Cl2, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

Alkoxybromination of olefins using ammonium bromide and oxone

A mild, efficient, and highly regio- and stereoselective method for the methoxy and ethoxy bromination of olefins has been developed using NH 4Br as a bromine source and Oxone as an oxidant. Various kinds of olefins (aromatic, linear, and cyclic olefins) afforded the corresponding alkoxy brominated products in moderate to excellent yields. Taylor & Francis Group, LLC.

Formation of quaternary stereogenic centers by copper-catalyzed asymmetric conjugate addition reactions of alkenylaluminums to trisubstituted enones

Alkenylaluminums undergo asymmetric copper-catalyzed conjugate addition (ACA) to β-substituted enones allowing the formation of stereogenic all-carbon quaternary centers. Phosphinamine-copper complexes proved to be particularly active and selective compared with phosphoramidite ligands. After extensive optimization, high enantioselectivities (up to 96 % ee) were obtained for the addition of alkenylalanes to β-substituted enones. Two strategies for the generation of the requisite alkenylaluminums were explored allowing for the introduction of aryl- and alkyl-substituted alkenyl nucleophiles. Moreover, alkyl-substituted phosphinamine (SimplePhos) ligands were identified for the first time as highly efficient ligands for the Cu-catalyzed ACA. Chiral synthesis made easy: The copper-catalyzed conjugate addition of alkenylaluminum reagents to 3-substituted cyclic enones allows for the formation of all-carbon chiral quaternary centers (see scheme; CuTC=copper(I) thiophene-2-carboxylate). Chiral phosphinamine (SimplePhos) ligands were found to be highly efficient for this transformation.