70090-82-3

Upstream product

• 350-51-6 3-fluorostyrene 
• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 463-51-4 Ketene 
• 89302-81-8 (3-fluorobenzyl)(triphenyl)phosphonium bromide 

Downstream Products

• 10557-18-3 1-(3-fluorophenyl)propane-1,2-dione 
• 456-48-4 3-Fluorobenzaldehyde 
• 324-15-2 2-(3-fluorophenyl)-1H-benzo[d]imidazole 
• 1311471-04-1 2-(3-fluorophenyl)-3-methylquinoxaline 
• 1171892-93-5 (E)-1-(3-ethoxyprop-1-enyl)-3-fluorobenzene 

Relevant academic research and scientific papers

Photoredox-Catalyzed α-Aminoalkylcarboxylation of Allenes with CO2

The photoredox-catalyzed α-aminoalkylcarboxylation of aryl allenes with CO2 and N,N-dimethylanilines is reported for the first time (26 examples, up to 96% yield). In the case of electron-deficient allenes, good regioselectivity was observed (up to 94:6), exclusively generating kinetic products over thermodynamic products. This protocol is a novel synthetic method for highly functionalized β,γ-unsaturated γ-aminobutyric esters.

Photochemical and Thermal Hydrations of Aromatic Allenes. Evidence for Allyl and Vinyl Cation Intermediates

The photohydration of aromatic allenes has been studied in water and in dilute aqueous sulfuric acid (0-25percent H2SO4).It was found that phenylallene (2a) and α-methylphenylallene (2b) undergo photohydration to give the corresponding cinnamyl alcohol derivatives.The proposed mechanism involves protonation of the central carbon of phenylallenes in their singlet excited state (S1).In contrast, (p-nitrophenyl)allene (2g) and (m-nitrophenyl)allene (2h) gave the corresponding (nitrophenyl)acetones.The mechanism for the formation of these ketones is believed to be due to initial protonation of the α- or γ-carbon atom of the (nitrophenyl)allene in the triplet excited state (T1).Phenylallenes with CN, CF3, and F substituents failed to photohydrate.The results of these photohydrations were compared with those of the much slower thermal hydrations in 70-83percent H2SO4.Phenylallenes 2a and 2b cyclized to the corresponding indene derivatives in 70percent H2SO4.Phenylallenes with NO2-substituents (2g-2h) underwent hydration to give the corresponding (nitrophenyl)acetones (expected products) and (nitrophenyl)-1-propanones (unexpected products) in 83percent H2SO4.Similar results were obtained with (m-cyanophenyl)allene.The formation of both types of ketone is discussed in terms of the intermediacy of a common vinyl cation intermediate.