70625-57-9

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 108-59-8 malonic acid dimethyl ester 
• 6639-19-6 N,N,2-trimethylbenzamide 
• 89-95-2 2-methyl-benzyl alcohol 
• 118-90-1 ortho-methylbenzoic acid 
• 69540-49-4 dimethyl o-bromomethyl-benzylidenemalononitrile 

Downstream Products

• 75950-75-3 3-(2'-methylphenyl)-(Z)-propenoic acid methyl ester 
• 70625-62-6 methyl (E)-3-(2-methylphenyl)-2-propenoate 
• 67-56-1 methanol 
• 69540-49-4 dimethyl o-bromomethyl-benzylidenemalononitrile 
• 1181669-45-3 2-(2-formylphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester 
• 1181669-44-2 2-(2-bromomethylphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester 
• 1181669-42-0 2-o-tolylcyclopropane-1,1-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

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.

Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes

Catalytic enantioselective [4+3] cycloaddition reaction betweeno-quinone methides and oxiranes was achieved by using a chiralN,N′-dioxide/TbIIIcomplex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%)

Electricity Driven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: a Mild and Straightforward Access to β-Hydroxy Ketones

An unprecedented external oxidant-free electrochemical protocol for 1, 3-oxohydroxylation of donor-acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π-electron cloud of the aryl ring to cleave the strained Csp3?Csp3 bond of cyclopropane to afford the β-hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.

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,

Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines

Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.

Enantioselective Catalyst Systems from Copper(II) Triflate and BINOL–Silanediol

Silanediol and copper catalysis are merged, for the first time, to create an enhanced Lewis acid catalyst system for enantioselective heterocycle functionalization. The promise of this silanediol and copper catalyst combination is demonstrated in the enantioselective addition of indoles to alkylidene malonates to give rise to the desirable adducts in excellent yield and high enantiomeric excess. From these studies, 1,1′-bi-2-naphthol (BINOL)-based silanediols emerge as one-of-a-kind cocatalysts. Their potential role in the reaction pathway is also discussed.

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.).

TiCl4 promoted formal [3 + 3] cycloaddition of cyclopropane 1,1-diesters with azides: Synthesis of highly functionalized triazinines and azetidines

A TiCl4 promoted formal [3 + 3] cycloaddition of cyclopropane 1,1-diesters with azides has been developed for the synthesis of highly functionalized triazinines. Both stoichiometric and substoichiometric versions of this reaction were accomplished dependent on the choice of solvent. It is noteworthy that the corresponding products could be easily converted to biologically important azetidines by simple thermolysis.

Domino synthesis of bridged bicyclic tetrahydro-1,2-oxazines: Access to stereodefined 4-aminocyclohexanols

Image Presented The intramolecular variant of the homo-[3 + 2]-dipolar cycloaddition of nitrones (generated in situ from an aldehyde and a hydroxylamine) with donor-acceptor cyclopropanes allows for the efficient synthesis of bridged tetrahydro-1,2-oxazines. This domino sequence produces adducts amenable to reductive N-O bond cleavage producing cis-1,4- aminocyclohexanols in excellent yields.

Thermal and photoinduced reduction of some benzyl bromides by an NAD(P)H model: The effect of electron withdrawing groups on mechanism and reactivity

A series of compounds, o-bromomethylbenzylidene-malononitrile (1), dimethyl o-bromomethyl-benzylidenemalonate (2) and methyl α-cyano-o-bromomethylcinnamate (3) were reduced in the dark and under irradiation by an NAD(P)H model, 1-benzyl-1,4-dihydronicotin