915288-76-5

Upstream product

• 637-69-4 4-Methoxystyrene 

Downstream Products

• 1354970-22-1 4-(4-bromophenyl)-1-[1-(4-methoxyphenyl)vinyl]-1H-1,2,3-triazole 
• 1374152-86-9 C₂₄H₂₁N₃O₃ 
• 1374152-91-6 C₂₄H₁₉Br₂N₃O₃ 
• 73402-86-5 2-phenyl-4-(4-methoxyphenyl)quinoline 
• 73744-44-2 2-fluoro-4'-methoxyacetophenone 
• 121194-35-2 3,3,3-trifluoro-1-(4-methoxyphenyl)propan-1-one 
• 2362-68-7 4-(4′-methoxyphenyl)-2-phenylthiazole 
• 315707-00-7 4-(4-methoxyphenyl)-N-(4-methlphenlyl)thiazol-2-amine 
• 21344-98-9 4-(4-methoxyphenyl)-N-phenyl-1,3-thiazol-2-amine 

Relevant academic research and scientific papers

Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides

A palladium-catalyzed cyclization of N-acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α-substituted vinyl azide serves as an internal nitrogen source. Also, C?H bond activation and C?N bond cleavage have been realized using hydrazone as directing group. (Figure presented.).

Access to Cycloalkeno[ c]-Fused Pyridines via Pd-Catalyzed C(sp2)-H Activation and Cyclization of N-Acetyl Hydrazones of Acylcycloalkenes with Vinyl Azides

A novel Pd(II)-catalyzed vinylic C-H activation and cyclization has been developed, reacting a series of small, medium, and large N-acetyl hydrazones of acylcycloalkenes with vinyl azides to access diverse cycloalkeno[c]-fused pyridine scaffolds. This protocol provides progress in C(sp2)-H bond activation of medium to large cycloalkenes, and the target products can be obtained in a specific regioselectivity with good functional group tolerance and a broad substrate scope.

Photoswitchable Regiodivergent Azidation of Olefins with Sulfonium Iodate(I) Reagent

Photoswitchable strategy for selective azidation of structurally diverse olefins under transition-metal-free conditions is reported. The unprecedented reactivity of trimethylsulfonium [bis(azido)iodate(I)] species under visible light allows radical azidooxygenation of the C═C πbond with distinctive selectivity. In the absence of visible light, the reaction proceeds through an ionic intermediate which led to complementary regioselectivity to provide α-alkyl azides. Mechanistic studies reveal that light-controlled regiodivergent azidation involving radical or an ionic pathway can be accomplished with exclusive regioselectivity.

Switchable reactivity between vinyl azides and terminal alkyne by nano copper catalysis

A novel nano copper-catalyzed substrate-dependent chemodivergent transformation of vinyl azides with a terminal alkyne is disclosed. 2,5-Disubstituted pyrroles were selectively obtained in high yield with aryl alkynes and aliphatic alkynes, whereas 2,3,4-trisubstituted pyrroles were formed with silylated alkynes. This switchable method provides a controllable and facile access to both multisubstituted pyrrole scaffolds with high efficiency, excellent regioselectivity, and good functional group compatibility.

Eosin Y- and Copper-Catalyzed Dark Reaction to Construct Ene-γ-Lactams

Eosin Y, a common organo-photocatalyst in visible-light photoredox processes, was found to show excellent catalytic activities for thermal redox reactions under a catalytic amount of Cu(OAc)2. With this catalytic system, vinyl azides and ketene silyl acetals combine to form formal [3 + 2] cycloadducts by α-ester radical addition without light irradiation. This method provides a mild and straightforward paradigm to prepare important synthons of five-membered ene-γ-lactams and bridge ring lactams. It is the first example of an eosin Y-catalyzed redox reaction in the dark.

[1+1+3] Annulation of Diazoenals and Vinyl Azides: Direct Synthesis of Functionalized 1-Pyrrolines through Olefination

A dirhodium carboxylate catalyzed [1+1+3] annulation reaction of diazoenals and vinyl azides that gives synthetically important enal-functionalized 1-pyrroline derivatives was developed. The reaction involves a novel rhodium-catalyzed olefination of diazoenals with vinyl azides via electrophilic enal carbenoids, resulting in a new class of enal acrylates. The annulation reaction was used for the direct synthesis of valuable deuterated 1-pyrrolines. Structural diversification of the enal-functionalized 1-pyrrolines resulted in the biologically important pyrrolidine-fused oxaziridine, amino acid derivatives, and a 6-azabicyclo[3.2.1]octane motif present in polycyclic alkaloids.

Electrochemical regioselective azidoiodination of alkenes

An efficient electrochemical approach to the vicinal iodoazides has been developed through constant current electrolysis of alkenes with NaN3and NaI in methanol. The reaction is proposed to proceed via a cyclic iodonium intermediate and thereby gives Markovnikov addition products exclusively.

Photoredox-catalysed redox-neutral trifluoromethylation of vinyl azides for the synthesis of α-trifluoromethylated ketones

A redox-neutral, mild, and simple protocol is developed for the synthesis of α-trifluoromethylated ketones from vinyl azides under transition-metal-free conditions. In the presence of organic photoredox catalyst N-methyl-9-mesityl acridinium and sodium trifluoromethanesulfinate, a broad range of substituted vinyl azides were found to react smoothly upon visible-light irradiation, readily furnishing the corresponding products in satisfied yields.

Lewis Acid Catalyzed Diastereoselective Cycloaddition Reactions of Donor-Acceptor Cyclopropanes and Vinyl Azides: Synthesis of Functionalized Azidocyclopentane and Tetrahydropyridine Derivatives

Lewis acid catalyzed [3 + 2]-cycloaddition reaction of donor-acceptor cyclopropanes with vinyl azides has been developed to obtain diastereomerically enriched azidocyclopentane derivatives. In addition, thermal chemoselective ring expansion of azidocyclopentanes to tetrahydropyridine derivatives and further diastereospecific reduction to a substituted piperidine derivative, with an excellent yield, was also achieved.

PIDA-I2 mediated direct vicinal difunctionalization of olefins: Iodoazidation, iodoetherification and iodoacyloxylation

Iodinium cation (I+ or IOAc) was produced from the combination of phenyliodine diacetate (PIDA) and iodine. I+ facilitated the direct vicinal difunctionalization of olefins to α-azido, α-trideuteriomethoxy, α-2,2,2-trifluoroethoxy and α-acyloxy alkyl iodides via cation-π interaction at room temperature and under transition-metal free conditions.