2976-01-4

Usage

Type of compound

ketone

Functional groups

furanyl and phenyl group attached to the first carbon atom of the propanone chain

Common uses

flavoring ingredient and fragrance in food and cosmetic industries, potential applications in pharmaceuticals and as a solvent in chemical processes

Safety precautions

may pose health and safety risks if not properly managed and used

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 88-14-2 2-furanoic acid 
• 3988-74-7 1-(2-furyl)-3-phenylpropen-1-one 
• 3988-74-7 (E)-1-(furan-2-yl)-3-phenylprop-2-en-1-one 
• 67-56-1 methanol 
• 13331-23-2 fur-2-ylboronic acid 
• 501-52-0 3-Phenylpropionic acid 
• 100-42-5 styrene 
• 615-08-7 2-furoic anhydride 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 100-52-7 benzaldehyde 
• 2786-02-9 2-lithiofuran 
• 645-45-4 hydrocinnamic acid chloride 
• 100-51-6 benzyl alcohol 

Downstream Products

• 118959-47-0 1-(β-Phenylethyl)-3,4-dihydropyrrolo<1,2-a>pyrazine 
• 120-92-3 cyclopentanone 
• 154538-13-3 3-hydroxy-2-(2-phenylethyl)pyridine 
• 859282-10-3 5-benzyl-4-(furan-2-yl)thiazol-2-amine 
• 1446018-10-5 5-benzyl-4-(furan-2-yl)-N-(4-methoxybenzyl)thiazol-2-amine 
• 118959-54-9 1-(β-Phenylethyl)-1,2,3,4-tetrahydropyrrolo<1,2-a>pyrazine 

Relevant academic research and scientific papers

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.

Method for catalyzing non-tension non-polar carbon-carbon single bond hydrogenolysis of dicarbonyl compound

The invention belongs to the technical field of chemical engineering, and particularly relates to a method for catalyzing non-tension non-polar carbon-carbon single bond hydrogenolysis of a dicarbonyl compound. According to the method, in a rare earth catalysis system, a secondary alcohol (amine) compound or hydrosilyane is used as a hydrogen source, and non-tension carbon-carbon single bonds of diketone and ketone ester are subjected to hydrogenolysis to form monoketone (ester). The method is a first carbon-carbon bond hydrogenolysis reaction of ketone, and the reaction has the advantages of good atom economy, high position selectivity and chemical selectivity, mild conditions, simplicity and convenience in operation, strong functional group tolerance and the like. Diketone and ketone ester are wide in source, and application is wide when diketone and ketone ester are converted into monoketone (ester).

Iron-catalyzed chemoselective hydride transfer reactions

A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

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.

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.

Electrochemical 1,4-reduction of α,β-unsaturated ketones with methanol and ammonium chloride as hydrogen sources

A sustainable, chemoselective 1,4-reduction of α,β-unsaturated ketones by means of an electrochemical method is presented, wherein the extremely inexpensive ammonium chloride (NH4Cl) is applied as the only additive. The reaction proceeds smoothly in the air at ambient temperature. Mechanistic studies reveal that both NH4Cl and solvent methanol work as hydrogen donors.

Arylation of Aldehydes to Directly Form Ketones via Tandem Nickel Catalysis

A nickel-catalyzed arylation of both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves α-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and β-hydrogen elimination.

C?C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KOtBu: Unusual Regioselectivity through a Radical Mechanism

We report a C?C bond-forming reaction between benzyl alcohols and alkynes in the presence of a catalytic amount of KOtBu to form α-alkylated ketones in which the C=O group is located on the side derived from the alcohol. The reaction proceeds under thermal conditions (125 °C) and produces no waste, making the reaction highly atom efficient, environmentally benign, and sustainable. Based on our mechanistic investigations, we propose that the reaction proceeds through radical pathways.

Nonbifunctional Outer-Sphere Strategy Achieved Highly Active α-Alkylation of Ketones with Alcohols by N-Heterocyclic Carbene Manganese (NHC-Mn)

The unusual nonbifunctional outer-sphere strategy was successfully utilized in developing an easily accessible N-heterocyclic carbene manganese (NHC-Mn) system for highly active α-alkylation of ketones with alcohols. This system was efficient for a wide range of ketones and alcohols under mild reaction conditions, and also for the green synthesis of quinoline derivatives. The direct outer-sphere mechanism and the high activity of the present system demonstrate the potential of nonbifunctional outer-sphere strategy in catalyst design for acceptorless dehydrogenative transformations.