395-21-1

Usage

Physical state

Colorless liquid

Molecular weight

208.26 g/mol

Uses

a. Organic synthesis
b. Building block for pharmaceutical and agrochemical compounds

Preparation method

Reaction of 1,4-diphenylbutadiyne with an appropriate fluoroalkylating agent

Significance

Useful intermediate in synthetic organic chemistry

Potential applications

Development of new materials and pharmaceuticals

Upstream product

• 917-64-6 methyl magnesium iodide 
• 345-83-5 4-fluorobenzophenone 
• 352-34-1 4-fluoro-1-iodobenzene 
• 155857-33-3 1--1-phenylethene 
• 339-23-1 1-(4-fluorophenyl)-1-phenylethan-1-ol 
• 100-42-5 styrene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 98-81-7 1-bromovinylbenzene 
• 1765-93-1 4-fluoroboronic acid 
• 14900-39-1 phenylvinylboronic acid 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 67300-99-6 1-phenylethenylmagnesium bromide 
• 98-86-2 acetophenone 
• 1159428-50-8 n-butyl(4-fluorophenyl)tellane 

Downstream Products

• 435-38-1 (+/-)-8-(4-fluoro-phenyl)-(4ar)-1,2,3,4,4a,5,6,7-octahydro-1t,4t-etheno-naphthalene-2t,3t,5t,6t-tetracarboxylic acid-2,3;5,6-dianhydride 
• 390-42-1 (E/Z)-3-(4-fluorophenyl)-3-phenylpropenoic acid 
• 47444-86-0 3-(4-fluoro-phenyl)-3-phenyl-acrylic acid-(2-diethylamino-ethyl ester) 
• 347-84-2 1-(4-fluorophenyl)-2-phenylethanone 
• 347-91-1 2-(4-fluorophenyl)-1-phenylethanone 
• 345-83-5 4-fluorobenzophenone 
• 362-86-7 3-(4-fluorophenyl)-3-phenylpropanoic acid 
• 942398-32-5 C₁₅H₁₁Br₂F 
• 1342713-28-3 2-(3-methylphenyl)-1-(4-fluorophenyl)-1-phenylethylene 
• 1342906-43-7 C₂₄H₂₅FO₅ 
• 1192278-61-7 1-fluoro-4-(1-phenylethyl)-benzene 
• 1420475-73-5 C₁₅H₁₅FO 

Relevant academic research and scientific papers

Rhodium-Catalyzed meta-Selective C?H Carboxylation Reaction of 1,1-Diarylethylenes via Hydrorhodation-Rhodium Migration

A meta-selective C?H carboxylation reaction of 1,1-diarylethylene derivatives with CO2 by using a rhodium catalyst with NaOiPr as a stoichiometric reductant has been achieved. Together with hydrogenation of the ethylene moiety, a carboxyl group was introduced to the meta-position of the aryl ring with high selectivity over the ortho-positions. Experimental and computational mechanistic studies indicate that this carboxylation reaction proceeds via hydrorhodation on the ethylene moiety, followed by 1,4-rhodium migration and successive 1,2-rhodium migration on the aryl ring. The use of a bulky phosphine ligand seems to be the key to this unusual aryl-to-aryl 1,2-rhodium shift.

Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams

A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.

Intermolecular [4 + 2] process of N-acyliminium ions with simple olefins for construction of functional substituted-1,3-oxazinan-2-ones

An efficient approach to functionalized 4,6-disubstituted-and 4,6,6-trisubstituted-1,3-oxazinan-2-ones skeleton has been developed through the reaction of semicyclic N,O-acetals 4a and 4b with 1,1-disubstituted ethylenes 5 or 8. As a result of such a [4 +

Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes

Photoinduced hydroarylation of alkenes is an appealing synthetic strategy for arene functionalization. Herein, we demonstrated that aryl radicals generated from electron-deficient aryl chlorides/bromides could be trapped by an array of terminal/internal aryl alkenes in the presence of [Pt(O^N^C^N)] under visible-light (410 nm) irradiation, affording anti-Markovnikov hydroarylated compounds in up to 95 % yield. Besides, a protocol for [Pt(O^N^C^N)]-catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4-dihydroquinolinones has been developed.

TMSOTf-mediated synthesis of skipped dienes through the addition of olefins to imines and semicyclicN,O-acetals

A novel approach to skipped dienes has been developed through the TMSOTf-mediated one-pot addition-substitution of olefins2a,2fand2gwith imines1a-1g, and a series of aryl substituted skipped dienes3aa-3gfwere accordingly obtained in 62%-94% yields. Moreov

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

Bimolecular vinylation of arenes by vinyl cations

Styrene derivatives can be easily synthesized from vinyl triflates and arenes under mild reaction conditions, using [Li][Al(OC(CF3)3)4] as a catalyst and LiHMDS as a base. This transformation is likely to involve a vinyl cation intermediate as an electrophile, which is corroborated by DFT calculations, deuterium-labeling and other control experiments. The use of an inert weakly coordinating anion is a decisive factor in this bimolecular vinylation process. This journal is

Deaminative carbonylative coupling of alkylamines with styrenes under transition-metal-free conditions

A transition-metal-free deaminative carbonylation of alkylamines with styrenes has been developed. The reaction shows good functional group compatibility and various α,β-unsaturated ketones were obtained in moderate to good yields. The alkyl radical generated from Katritzky salts via base-promoted C-N bond cleavage is one of the key intermediates in this reaction. This journal is

Iodobenzene-catalyzed oxidative cleavage of olefins to carbonyl compounds

A metal-free approach for the oxidative cleavage of carbon–carbon double bonds of olefins to carbonyl compounds was established by using oxidant m-CPBA and non-metallic organocatalyst PhI in toluene/H2O. A broad scope of aromatic olefins was used. All the reactions proceeded smoothly at 35 °C in short reaction time to furnish the respective mono- and double carbonyl compounds selectively in moderate to good yields.

Cu/Ni-Catalyzed Cyanomethylation of Alkenes with Acetonitrile for the Synthesis of β,γ-Unsaturated Nitriles

We have developed a protocol for the Cu/Ni-catalyzed cyanomethylation of alkenes with acetonitrile for the synthesis of β,γ-unsaturated nitriles. This is the first example of a direct coupling of the alkene sp2 C - H bond and the acetonitrile sp3 C - H bond for the preparation of β,γ-unsaturated nitriles. Acetonitrile, an inexpensive and stable solvent, is demonstrated to be a useful cyanomethyl source. The combination of copper and nickel catalysts resulted in a high reaction efficiency.