2248-13-7

Usage

Uses

Used in Organic Synthesis:
4-(4-Fluorophenyl)-1-butene is used as a building block in organic synthesis for the creation of various organic compounds. Its fluorophenyl group provides unique reactivity and selectivity, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research:
In the field of research, 4-(4-Fluorophenyl)-1-butene serves as a model compound for studying the effects of fluorination on the chemical and physical properties of organic molecules. Its use aids in understanding the influence of fluorine substitution on molecular behavior, which is crucial for the development of new materials and compounds with tailored properties.
Used in Pharmaceutical Industry:
4-(4-Fluorophenyl)-1-butene is used as an intermediate in the pharmaceutical industry for the synthesis of drug candidates. The presence of the fluorine atom can significantly alter the pharmacokinetic and pharmacodynamic properties of the resulting compounds, potentially leading to improved drug efficacy and safety.
Used in Agrochemical Industry:
In the agrochemical industry, 4-(4-Fluorophenyl)-1-butene is utilized as a precursor for the development of new pesticides and herbicides. The introduction of the fluorine atom can enhance the lipophilicity and metabolic stability of these compounds, resulting in more effective and environmentally friendly agrochemicals.

InChI:InChI=1/C10H11F/c1-2-3-4-9-5-7-10(11)8-6-9/h2,5-8H,1,3-4H2

Upstream product

• 106-95-6 allyl bromide 
• 84648-52-2 C₁₈H₁₆ClFO₄ 
• 106-99-0 buta-1,3-diene 
• 352-13-6 4-flourophenylmagnesium bromide 
• 2622-05-1 allylmagnesium bromide 
• 459-46-1 4-Fluorobenzyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 459-57-4 4-fluorobenzaldehyde 
• 591-87-7 Allyl acetate 
• 401514-49-6 [(4-fluorophenyl)methylidene]hydrazine 
• 459-51-8 1-fluoro-4-(fluoromethyl)benzene 
• 762-72-1 allyl-trimethyl-silane 
• 459-31-4 3-(4-fluorophenyl)propanoic acid 
• 702-15-8 3-(4-fluorophenyl)propan-1-ol 

Downstream Products

• 109635-75-8 [4-(4-fluorophenyl)butyl]phosphinic acid 
• 1214320-52-1 (Z)-triethyl(4-(4-fluorophenyl)but-1-enyl)silane 
• 1214320-65-6 (E)-triethyl(4-(4-fluorophenyl)but-1-enyl)silane 
• 1267588-86-2 C₂₄H₂₀FNO₃S 
• 1267588-73-7 C₂₄H₂₀FNO₃S 
• 20651-65-4 4-(n-butyl)fluorobenzene 
• 24484-22-8 5-(4-fluorophenyl)-pentanoic acid 
• 222640-88-2 1-(but-2-en-1-yl)-4-fluorobenzene 

Relevant academic research and scientific papers

Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis

Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).

Controllable Isomerization of Alkenes by Dual Visible-Light-Cobalt Catalysis

We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization.

Phosphorus Coordination Chemistry in Catalysis: Air Stable P(III)-Dications as Lewis Acid Catalysts for the Allylation of C-F Bonds

Modification of C-F bonds with main-group catalysts has typically employed electron-deficient Lewis superacids in high oxidation states, and the challenges of preparing and handling such species have prevented broader adoption of metal-free reduction protocols. Here, we show that a hemilabile ligand coordinated to an easily accessed P(III) center imparts air stability without sacrificing the ability to activate C-F bonds. Catalytic C-C coupling of benzyl fluorides with allylsilanes was achieved using a P(III) complex under benchtop conditions. This application of coordination chemistry principles to main-group Lewis acids reveals a new strategy for controlling catalysis.

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Palladium-Catalyzed Electrochemical Allylic Alkylation between Alkyl and Allylic Halides in Aqueous Solution

A new route for the direct cross-coupling of alkyl and allylic halides using electrochemical technique has been developed in aqueous media under air. Catalyzed by Pd(OAc)2, the Zn-mediated allylic alkylations proceed smoothly between a full range of alkyl halides (primary, secondary, and tertiary) and substituted allylic halides. Protection-deprotection of acidic hydrogen in the substrates is avoided.

Monocarboxylation and intramolecular coupling of butenylated arenes via palladium-catalyzed C-H activation process

A novel and practical reaction for the direct intramolecular oxidative coupling of butenylated arenes is reported. With the catalysis of Pd(OAc)2, reactions of various butenylated arenes and carboxylic acids with Selectfluor reagent in CH3CN solution afforded the corresponding monocarboxylation/cyclization products in good yields under mild conditions. This research demonstrated an economic method with the synthesis of 2-tetralyl carboxylic esters, a valuable class of bioactive compounds.

Wacker-type oxidation and dehydrogenation of terminal olefins using molecular oxygen as the sole oxidant without adding ligand

An efficient and economical palladium-catalyzed oxidation system has been identified. The oxidation system, characterized by not adding ligand and using molecular oxygen as the sole oxidant, can realize the Tsuji-Wacker oxidation of terminal olefins and especially styrenes to methyl ketones; in addition, this system can achieve tandem Wacker oxidation-dehydrogenation of terminal olefins to α,β-unsaturated ketones.

Chemo-, regio-, and stereoselective iron-catalysed hydroboration of alkenes and alkynes

The highly chemo-, regio-, and stereoselective synthesis of alkyl- and vinyl boronic esters with good functional group tolerance has been developed using in situ activation of a bench-stable iron(ii) pre-catalyst and pinacolborane (16 examples, 45-95% yield, TOF up to 30000 mol h-1). The first iron-catalysed alkene hydrogermylation is also reported.

Picosecond radical kinetics. Rate constants for ring openings of 2-aryl-substituted cyclopropylcarbinyl radicals

The kinetics of ring openings of a series of eight (trans-2-arylcyclopropyl)methyl radicals (1) were studied by indirect kinetic methods using Barton's PTOC esters as radical precursors and reaction with PhSeH as the competition reaction. The substituents were CF3, F, Me, and OMe located on both the para and meta positions of the aromatic ring. Syntheses of the radical precursors and the products of the radical reactions are described. Kinetics were determined between -43 and 25°C in four cases (CF3 and OMe substituents) and at 0 and 25°C in the other four cases. The rate constants at 25°C ranged from 1.0 x 1011 s-1 (p-CH3) to 4.1 x 1011 s-1 (p-CF3). The relatively large acceleration of the p-CF3 group, ca. 2.5 times as fast as the parent system with Ar = Ph, correlates well with Adam's ΔD substituent parameters but not with other radical substituent parameters. These calibrated radical rearrangements provide a new set of ultrafast reactions that can be applied in mechanistic probe studies.

COMPLEXES OF TRANSITION METALS IN THE CHEMISTRY OF CONJUGATED SYSTEMS. III. REACTION OF DIENE HYDROCARBONS WITH ORGANOMAGNESIUM COMPOUNDS IN THE PRESENCE OF SALTS AND COMPLEXES OF TRANSITION METALS

The effect of the structure of the reagents and the nature of the catalyst on the direction and selectivity in the reaction of 1,3-dienes and their derivatives with aromatic Grignard reagents was investigated.It was shown that in the presence of salts and complexes of iron(III) 1,3-alkadienes R1CH=C(R2)C(R3)=CH2 react with arylmagnesium halides to form trans-(E)-1-aryl-1,3-alkadienes, whereas the sterically hindered (R2, R3=CH3) cyclic 1,3-alkadienes and also 1,2-alkadienes give mainly adducts (1:1).Catalysis by the phosphine complexes of nickel(II) leads to the formation of telomeric (2:1) (E)-1-aryl-2,7- and (E,E)-1-aryl-2,6-alkadienes.The results demonstrate the determining role of the stereochemical conditions for the coordination of the diene in the course of the reaction and also the significant contribution from the processes of one-electron reduction of the catalyst.