42122-27-0

Upstream product

• 186581-53-3 diazomethane 
• 25294-65-9 3-(4-bromophenyl)-2-propynoic acid 
• 67-56-1 methanol 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 201230-82-2 carbon monoxide 
• 84750-93-6 1,1-difluoro-2-(4-bromophenyl)ethene 
• 1200-07-3 trans-4-bromocinnamic acid 
• 112595-55-8 (2RS,3SR)-2,3-dibromo-3-(4-bromophenyl)propanoic acid 
• 589-87-7 1,4-bromoiodobenzene 
• 922-67-8 propynoic acid methyl ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 952569-45-8 2,3-dibromo-3-(4-bromophenyl)-propionic acid ethyl ester 
• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 
• 126629-81-0 methyl 3-(4-bromophenyl)-3-oxopropanoate 

Downstream Products

• 367928-57-2 5-(4-bromo-phenyl)-1,2-dihydro-pyrazol-3-one 
• 137201-67-3 E-methyl β-morpholino-p-bromocinnamate 
• 137201-71-9 E-methyl β-(N,N-diethylamino)-p-bromocinnamate 
• 1088410-99-4 3-(4-bromophenyl)-1-methylpyrrolidine 

Relevant academic research and scientific papers

De Novo Construction of Substituted Terephthalates via Phosphine Catalyzed Domino Benzannulation Reactions

The robustness of phosphine catalysis enabling the domino benzannulation reactions of allenoates with enamines is described. A broad array of substituted terephthalates were delivered under simple and practical reaction conditions. Furthermore, the reaction could be carried out on a gram scale with higher yield, and various conversions of the terephthalate products demonstrate the versatility of this transformation. (Figure presented.).

Synthesis method of aryl-substituted alkyne

The invention relates to the technical field of synthesis of aryl substituted alkyne, and discloses a synthetic method of an aryl-substituted alkyne, and discloses a synthesis method of an aryl-substituted alkyne. Aryl boronic acid and divalent copper compounds, 8 - hydroxyquinoline, an oxidizing agent and an inorganic base are added to the reaction solvent, and the aryl substituted alkyne is obtained by stirring and separating after stirring at room temperature. Compared with the existing sonogashira reaction, the synthesis method disclosed by the invention realizes the aryl reaction of the lean electron alkyne through the oxidative coupling reaction, avoids Sonogashira reaction required precious palladium catalyst, can react at room temperature, and is mild in reaction condition and high in product yield.

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

Enantioselective Fluorination of α-Branched β-Ynone Esters Using a Cinchona-Based Phase-Transfer Catalyst

Herein, we report the fluorination of α-branched β-ynone esters to afford their corresponding quaternary fluorinated products with good enantioselectivity (ee = 73-90%) using a cinchona-based phase-transfer catalyst. α-Branched β-ynone esters possess a highly acidic α-proton and form their corresponding enolate as a single isomer, which allows the enantioselective fluorination reaction to occur under standard cinchona-based phase-transfer catalyst conditions. Moreover, the obtained α-fluorinated product can be treated with [(SPhos)AuNTf2] (1 mol %) to afford a fluorinated 3,5-diketo carboxylic acid.

Organocatalytic trans Phosphinoboration of Internal Alkynes

We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P-Bpin are efficiently converted into the corresponding trans-α-phosphino-β-boryl acrylate products in moderate to good yield with high regio- and Z-selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only a modest excess of the phosphinoboronate. X-ray crystallography experiments allowed structural assignment of the unprecedented and densely functionalized (Z)-α-phosphino-β-boryl acrylate products.

Synthesis of 1-Amino-2 H-quinolizin-2-one Scaffolds by Tandem Silver Catalysis

An efficient tandem cycloisomerization-amination reaction catalyzed by silver is described. This rapid and atom-economic reaction delivered 1-amino-2H-quinolizin-2-one scaffolds in high yields under mild conditions. The reaction could be extended to an asymmetric version albeit with moderate enantioselective excess of the products. In addition, the products can be easily reduced into various azabicycles containing 4-pyridones, which are important building blocks in organic synthesis.

Trans-Hydroboration of Propiolamides: Access to Primary and Secondary (E)-β-Borylacrylamides

A base-mediated trans-hydroboration of propiolamides that provides access to previously elusive primary and secondary (E)-β-borylacrylamide products has been developed. In the presence of n-butyllithium and pinacolborane, complete regioselectivity and ste

Cobalt(III)-Catalyzed Intermolecular Carboamination of Propiolates and Bicyclic Alkenes via Non-Annulative Redox-Neutral Coupling

A cobalt(III)-catalyzed, redox-neutral, intermolecular carboamination of propiolates and bicyclic alkenes was developed. This non-annulative coupling strategy features atom economy, high regioselectivity, good yields, and functional groups tolerance. Such a carboamination reaction was applied to modified phenols from the corresponding phenols under mild conditions.

Trans -Hydroboration vs. 1,2-reduction: Divergent reactivity of ynones and ynoates in Lewis-base-catalyzed reactions with pinacolborane

Ynones and ynoates react with pinacolborane in a divergent manner in the presence of nucleophilic phosphine catalysts. Ynones are transformed to the corresponding propargyl alcohols in good yields with high regio- and chemoselectivity. Ynoates undergo highly regio- and stereoselective trans-hydroboration to produce E-vinylboronates. Impressive divergence in reactivity of ynones and ynoates can be traced back to the mechanistic aspects of 1,2-reduction and trans-hydroboration. A comparative analysis of the two pathways paints a complex picture in which different reaction rates control selectivity in these seemingly unrelated processes and explains how sufficiently acidic protons in the reaction mixtures can be used to steer the selectivity in different directions.