52927-45-4

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 108-59-8 malonic acid dimethyl ester 
• 108-24-7 acetic anhydride 
• 18469-37-9 4-bromo-N,N-dimethylbenzamide 

Downstream Products

• 696613-64-6 2-[1-(4-bromo-phenyl)-2-(4-chloro-benzoyl)-butyl]-malonic acid dimethyl ester 
• 911448-78-7 dimethyl 2-[1-(4-bromophenyl)-3-(4-methylphenyl)-3-oxo-2-phenylpropyl]malonate 
• 1116152-89-6 (R)-dimethyl 2-[1-(4-bromophenyl)-2-(furan-2-yl)-2-oxoethyl]malonate 
• 851293-09-9 dimethyl 2-(4-bromophenyl)cyclopropane-1,1-dicarboxylate 
• 1398508-09-2 dimethyl 2‐{(S)‐(4‐bromophenyl)[(1S)‐2‐oxocyclohexyl]methyl}propanedioate 
• 1310576-72-7 trimethyl (2R,3R,5R)-3-(4-bromophenyl)-5-(4-chlorophenyl)pyrrolidine-2,4,4-tricarboxylate 

Relevant academic research and scientific papers

Reductive Knoevenagel Condensation with the Zn-AcOH System

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.

Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step

We describe a visible-light-promoted addition of a hydrogen atom and an acetal carbon toward various electron-deficient alkenes. 1,3-Dioxolane is converted to its radical species in the presence of persulfate and an iridium catalyst upon visible light irradiation, which then reacts with electron-deficient alkenes. The reaction operates via a radical chain mechanism, a less commonly observed pathway for this class of transformation. Hydrogen atom transfer from 1,3-dioxolane to α-malonyl radicals is corroborated by experimental and density functional theory studies.

Amides as surrogates of aldehydes for C-C bond formation: amide-based direct Knoevenagel-type condensation reaction and related reactions

Aldehydes are perhaps the most versatile compounds that enable many C-C bond forming reactions, which are not amenable for other subclasses of carbonyl compounds. We report the first use of amides as surrogates of aldehydes for C-C bond formation, namely,

Synthesis and highly potent anti-inflammatory activity of licofelone- and ketorolac-based 1-arylpyrrolizin-3-ones

Since NSAIDs are commonly used anti-inflammatory agents that produce adverse effects, there have been ongoing efforts to develop more effective and less toxic compounds. Based on the structure of the anti-inflammatory pyrrolizines licofelone and ketorolac

An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters

A synthetic route to trans-configured tetrahydrothiophenes (THTs) through Fe(OTf)3-promoted [3+2] cycloaddition of donor–acceptor cyclopropanes with thionoesters was developed. The cycloaddition proceeded in high yield with high diastereoselectivity, affording transient α-alkoxy THTs. Not only aromatic and aliphatic thionoesters, but also thionolactone were applicable to the present iron catalysis. Further transformation of the S,O-ketal functionality of the product was achieved in a highly trans diastereoselective manner. Moreover, the utility of our methodology was clearly demonstrated by the synthesis of enantioenriched trans-configured THTs.

Intermolecular Reductive Couplings of Arylidene Malonates via Lewis Acid/Photoredox Cooperative Catalysis

A cooperative Lewis acid/photocatalytic reduction of arylidene malonates yields a versatile radical anion species. This intermediate preferentially undergoes intermolecular radical-radical coupling reactions, and not the conjugate addition-dimerization reactivity typically observed in the single-electron reduction of conjugate acceptors. Reported here is the development of this open-shell species in intermolecular radical-radical cross couplings, radical dimerizations, and transfer hydrogenations. This reactivity underscores the enabling modularity of cooperative catalysis and demonstrates the utility of stabilized enoate-derived radical anions in intermolecular bond forming reactions.

Scandium(III) Trifluoromethanesulfonate Catalyzed Selective Reactions of Donor–Acceptor Cyclopropanes with 1,1-Diphenylethanols: An Approach to Polysubstituted Olefins

An unexpected synthetic approach to polysubstituted olefins through the scandium(III) trifluoromethanesulfonate catalyzed ring-opening reaction of donor–acceptor cyclopropanes with 1,1-diphenylethanols was developed. The reactions, which are experimentally easy to handle, feature tolerance of various functional groups and mild reaction conditions. On the basis of experimental evidence, a plausible mechanism was also proposed.

Cascade One-Pot Synthesis of Indanone-Fused Cyclopentanes from the Reaction of Donor-Acceptor Cyclopropanes and Enynals via a Sequential Hydrolysis/Knoevenagel Condensation/[3+2] Cycloaddition

A cascade reaction of donor-acceptor cyclopropanes with enynals to construct indanone-fused cyclopentanes via a sequential hydrolysis/Knoevenagel condensation/[3+2] cycloaddition is reported. The desired indanone-fused cyclopentanes were obtained in good yields. This method features mild reaction conditions and broad substrate scope, which render it very appealing to chemists for the synthesis of complex molecules containing an indanone-fused cyclopentane moiety. Moreover, the products could be further converted into compounds with different functional groups through the well-known transformations. (Figure presented.).

Triflic Acid Catalyzed Formal [3 + 2] Cycloaddition of Donor-Acceptor Oxiranes and Nitriles: A Facile Access to 3-Oxazolines

A TfOH-catalyzed chemoselective [3 + 2] cycloaddition of donor-acceptor oxiranes and nitriles is described. This reaction provides an efficient and practical method for the preparation of useful 3-oxazolines in good to excellent yields (up to 99%).

Synthesis of 3-Oxazolines via SnCl4-Promoted Formal [3+2] Cycloaddition of Donor-Acceptor Oxiranes and Nitriles

A novel SnCl4-promoted formal [3+2] cycloaddition of donor-acceptor oxiranes and nitriles via chemoselective C-C bond breakage was developed. This reaction provides an efficient and practical method for the preparation of 3-oxazolines in good yields (up to 89%).