4098-17-3

Upstream product

• 100-42-5 styrene 

Downstream Products

• 1499-00-9 2-phenylaziridine 
• 618-36-0 rac-methylbenzylamine 
• 1354970-13-0 4-butyl-1-(1-phenylvinyl)-1H-1,2,3-triazole 
• 1354970-15-2 4-(4-bromophenyl)-1-(1-phenylvinyl)-1H-1,2,3-triazole 
• 1354970-16-3 4-benzyl-1-(1-phenylvinyl)-1H-1,2,3-triazole 
• 1354970-17-4 4-(3-chloropropyl)-1-(1-phenylvinyl)-1H-1,2,3-triazole 
• 1354970-18-5 4-[1-(1-phenylvinyl)-1H-1,2,3-triazol-4-yl]butan-1-ol 
• 55324-08-8 4-phenyl-1-(1-phenylvinyl)-1H-1,2,3-triazole 
• 709-21-7 3,3,3-trifluoro-1-phenylpropan-1-one 
• 4546-48-9 methyl 2-phenylquinoline-4-carboxylate 
• 450-95-3 2-fluoroacetophenone 
• 70-11-1 α-bromoacetophenone 

Relevant academic research and scientific papers

Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates

The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.

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.

Electrochemical synthesis of enaminones: Via a decarboxylative coupling reaction

An environmentally benign and efficient electrochemical synthesis of enaminones via a decarboxylative coupling reaction of α-keto acids using n-Bu4NI as a redox catalyst and electrolyte under constant current electrolysis in an undivided cell is reported. A broad vinyl azide substrate scope and high functional group tolerance are observed. A gram-scale reaction further demonstrates the practicability of the protocol. The results of cyclic voltammetry and control experiments indicate that I2 is likely the active species to initiate the oxidative decarboxylation via an acyl hypoiodite intermediate.

[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.

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.

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.

Unexpected Direct Synthesis of N-Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition

The unexpected synthesis of industrially important N-vinyl amides directly from aldehydes and α,β-unsaturated N-vinyl amides from esters is reported. This reaction probably proceeds through an initial [3+2] azide–enolate cycloaddition involving a vinyl azide generated in situ. A survey of the reaction scope and preliminary mechanistic findings supported by quantum computational analysis are reported, with implications for the future development of atom-efficient amide synthesis. Intriguingly, this study suggests that (cautious) reevaluation of azidoethene as a synthetic reagent may be warranted.

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.

[3+2] Annulation of Donor-Acceptor Cyclopropanes with Vinyl Azides

A Sc(OTf)3-catalyzed reaction of vinyl azides with donor-acceptor cyclopropanes affords highly functionalized azidocyclopentanes in a diastereoselective fashion. The resulting azidocyclopentanes could be transformed into various cyclic scaffolds.

Iodoazidation of Alkenes by Using Iodine Pentafluoride-Pyridine-Hydrogen Fluoride and Trimethylsilyl Azide

Iodoazidation of alkenes was carried out by using iodine pentafluoride-pyridine-hydrogen fluoride and trimethylsilyl azide. In the reactions of terminal alkenes, anti-Markovnikov products were formed selectively. Cyclohexene gave a mixture of cis- and trans-adducts. These results suggest the involvement of radical species in the reaction.