41938-64-1

Usage

Uses

Used in Pharmaceutical Synthesis:
4'-Fluoro-3-phenylpropiophenone is used as a key intermediate for the production of various pharmaceuticals and related compounds. Its unique structure, including the fluorine atom and phenyl group, contributes to the development of new drugs with improved properties.
Used in Organic Synthesis:
In the field of organic synthesis, 4'-Fluoro-3-phenylpropiophenone serves as a versatile building block for creating a wide range of organic compounds. Its reactivity and structural features make it valuable for synthesizing complex organic molecules.
It is crucial to handle 4'-Fluoro-3-phenylpropiophenone with care and adhere to proper safety protocols due to its potential hazards, ensuring the safety of both individuals and the environment during its use in research and industrial applications.

InChI:InChI=1/C15H13FO/c16-14-9-7-13(8-10-14)15(17)11-6-12-4-2-1-3-5-12/h1-5,7-10H,6,11H2

Upstream product

• 22966-25-2 (E)-1-(4-fluorophenyl)-3-phenyl-2-propen-1-one 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 347-93-3 3-chloro-4'-fluoropropiophenone 
• 98-80-6 phenylboronic acid 
• 134747-51-6 C₁₅H₁₃FO 
• 73183-34-3 bis(pinacol)diborane 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 100-42-5 styrene 
• 456-22-4 4-Fluorobenzoic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 1765-93-1 4-fluoroboronic acid 
• 331987-63-4 1-(4-fluorobenzoyl)pyrrolidine-2,5-dione 

Downstream Products

• 838-63-1 1-(4-fluorophenyl)-3-phenyl-1-propanol 
• 105222-20-6 3-(4-fluorophenyl)-1H-indene 
• 5262-62-4 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1,2-oxazole 
• 1018186-48-5 5-benzyl-4-(4-fluorophenyl)thiazol-2-amine 
• 1621006-55-0 2-bromo-1-(4-fluorophenyl)-3-phenylpropan-1-one 
• 1446018-11-6 5-benzyl-4-(4-fluorophenyl)-N-(4-methoxybenzyl)thiazol-2-amine 

Relevant academic research and scientific papers

Nickel-catalyzed α-alkylation of ketones with benzyl alcohols

We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

Application of 4, 6-dimethyl-2-mercaptopyrimidine bivalent nickel complex in preparation of [alpha]-alkyl ketone

The invention relates to the field of metal organic chemistry, in particular to application of a 4, 6-dimethyl-2-mercaptopyrimidine bivalent nickel complex in preparation of [alpha]-alkyl ketone, which takes a 4, 6-dimethyl-2-mercaptopyrimidine nickel (II) compound as a catalyst and realizes selective preparation of [alpha]-alkyl ketone through cross-coupling reaction of secondary alcohol and primary alcohol by regulating and controlling reaction conditions. The coupling reaction is carried out in anhydrous toluene in the presence of alkali under the protection of inert gas. The application has the advantages of mild reaction system conditions and wide substrate applicability, and effectively avoids the use of organic phosphine ligands and noble metals.

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Direct conversion of secondary propargyl alcohols into 1,3-di-arylpropanoneviaDBU promoted redox isomerization and palladium assisted chemoselective hydrogenation in a single pot operation

Palladium(ii)acetate is found to be an efficient catalyst for the single-step conversion of secondary propargyl alcohols to 1,3-diarylpropanone derivatives under mild basic conditions. The reaction is believed to proceedviaredox isomerisation of secondary propargyl alcohols followed by chemoselective reduction of an enone double bond with formic acid as an adequate hydrogen donor. A large number of 1,3-diarylpropanone derivatives may readily be prepared from a milligram to a multigram scale.

Electrochemical-Induced Hydrogenation of Electron-Deficient Internal Olefins and Alkynes with CH3OH as Hydrogen Donor

Efficient hydrogenation of electron-deficient internal olefins and alkynes access to saturate ketone with CH3OH as a single hydrogen donor under electrochemical conditions has been successfully developed. This hydrogenation strategy can be used to convert electron-deficient internal olefins and alkynes to saturate ketone under electrochemical conditions with exogenous-reductant and a metal catalyst. Mechanistic studies reveal that radical hydrogenation was involved in this transformation. Notably, various electron-deficient internal olefins and alkynes could be tolerated in such an electrochemical hydrogenation synthetic strategy and can be easily scaled up with good efficiency. (Figure presented.).

Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines

Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.

Cu(I) mediated hydrogen borrowing strategy for the α-alkylation of aryl ketones with aryl alcohols

Abstract: New triazolium Schiff bases (TSBs) were synthesised via a simple and high throughput process. The new salts were successfully characterised. When reacted with Cu(CH3CN)4PF6, the TSB salts formed mononuclear triazole Schiff base copper(I) complexes and dinuclear complexes that were also characterised. The?copper complexes were generated in situ (mixtures of TSB salts with Cu(CH3CN)4PF6) and applied as homogeneous catalysts for the C–C coupling of a variety of aryl ketones with aryl alcohols, from which?significant reactivity was observed. Reaction conditions were optimised, and the results indicate that the catalyst systems are very robust. A catalyst concentration of 10?mol% efficiently and selectively catalysed the α-alkylation of methyl phenyl ketone and its derivatives to afford up to 94% yield of 1,3-diphenylpropan-1-one and its analogues. The process is adaptable with analogues of acetophenone and benzyl alcohol bearing various regulating substituents tolerated. Graphic abstract: [Figure not available: see fulltext.].

Sustainable and Selective Alkylation of Deactivated Secondary Alcohols to Ketones by Non-bifunctional Pincer N-heterocyclic Carbene Manganese

A sustainable and green route to access diverse functionalized ketones via dehydrogenative–dehydrative cross-coupling of primary and secondary alcohols is demonstrated. This borrowing hydrogen approach employing a pincer N-heterocyclic carbene Mn complex displays high activity and selectivity. A variety of primary and secondary alcohols are well tolerant and result in satisfactory isolated yields. Mechanistic studies suggest that this reaction proceeds via a direct outer-sphere mechanism and the dehydrogenation of the secondary alcohol substrates plays a vital role in the rate-limiting step.

Chelate ring size effects of Ir(P,N,N) complexes: Chemoselectivity switch in the asymmetric hydrogenation of α,β-unsaturated ketones

A novel, highly modular approach has been developed for the synthesis of new chiral P,N,N ligands with the general formula Ph2P(CH3)CH(CH2)mCH(CH3)NHCH2CH2(CH2)nN(CH3)2 and Ph2P(CH3)CHCH2CH(CH3)NHCH2(CH2)n-2-Py (m, n = 0, 1). The systematic variation of their P–N and N–N backbone led to the conclusion that the activity, chemo- and enantioselectivity in the hydrogenation of α,β-unsaturated ketones are highly dependent on the combination of the two bridge lengths. It has been found that a minor change in the ligand's structure, i. e. varying the value of m from 1 to 0, can switch the chemoselectivity of the reaction, from 80percent C[dbnd]O to 97percent C[dbnd]C selectivity.