1802-36-4

Usage

Physical state

Colorless liquid

Odor

Sweet, floral smell

Uses

Flavoring agent in food and beverage industry; production of fragrances and perfumes; synthesis of pharmaceuticals and other organic compounds

Hazards

Flammable; may cause irritation to skin, eyes, and respiratory system if not properly handled

Upstream product

• 100-54-9 pyridine-3-carbonitrile 
• 103-63-9 1-phenyl-2-bromoethane 
• 626-55-1 3-Bromopyridine 
• 63888-20-0 3-phenyl-1-propen-1-yl acetate 
• 500-22-1 3-pyridinecarboxaldehyde 
• 264625-65-2 3-(azidomethyl)-2-phenylpyridine 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 
• 1120-90-7 3-iodopyridine 
• 104-53-0 3-phenyl-propionaldehyde 
• 350-03-8 methyl-3-pyridylketone 
• 100-51-6 benzyl alcohol 
• 100-55-0 3-hydroxymethylpyridin 
• 536-74-3 phenylacetylene 
• 144825-44-5 (+/-)-tert-butyl 1-(pyridin-3'-yl)prop-2-en-1-yl carbonate 

Downstream Products

• 1802-34-2 4-(3-phenylpropyl)-pyridine 

Relevant academic research and scientific papers

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.

Nickel-Catalyzed Alkylation of Ketone Enolates: Synthesis of Monoselective Linear Ketones

Herein we have developed a Ni-catalyzed protocol for the synthesis of linear ketones. Aryl, alkyl, and heteroaryl ketones as well as alcohols yielded the monoselective ketones in up to 90% yield. The catalytic protocol was successfully applied in to a gram-scale synthesis. For a practical utility, applications of a steroid derivative, oleyl alcohol, and naproxen alcohol were employed. Preliminary catalytic investigations involving the isolation of a Ni intermediate and defined Ni-H species as well as a series of deuterium-labeling experiments were performed.

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.

Switchable Chemoselective Transfer Hydrogenations of Unsaturated Carbonyls Using Copper(I) N-Donor Thiolate Clusters

Unsaturated alcohols and saturated carbonyls are important chemical, pharmaceutical, and biochemical intermediates. We herein report an efficient transfer hydrogenation protocol in which conversion of unsaturated carbonyl compounds to either unsaturated alcohols or saturated carbonyls was catalyzed by Cu(I) N-donor thiolate clusters along with changing hydrogen source (isopropanol or butanol) and base (NaOH or K2CO3). Mechanistic studies supported by DFT transition state modeling indicate that such a chemoselectivity can be explained by the relative concentrations of Cu(I) monohydride and protonated Cu(I) hydride complexes in each catalytic system.

Cobalt-Catalyzed α-Alkylation of Ketones with Primary Alcohols

An ionic cobalt-PNP complex is developed for the efficient α-alkylation of ketones with primary alcohols for the first time. A broad range of ketone and alcohol substrates were employed, leading to the isolation of alkylated ketones with yields up to 98%. The method was successfully applied to the greener synthesis of quinoline derivatives while using 2-aminobenzyl alcohol as an alkylating reagent.

Manganese-Catalyzed Hydrogen-Autotransfer C?C Bond Formation: α-Alkylation of Ketones with Primary Alcohols

A novel catalytic hydrogen-autotransfer protocol for the atom-efficient α-alkylation of ketones with readily available alcohols is presented. The use of manganese complexes bearing non-innocent PNP pincer ligands enabled the functionalization of a broad range of valuable ketones, including 2-oxindole, estrone 3-methyl ether, and testosterone. Mechanistic investigations suggest the participation of an intramolecular amidate-assisted alcohol-dehydrogenation process.

Replacing a stoichiometric silver oxidant with air: Ligated Pd(II)-catalysis to β-aryl carbonyl derivatives with improved chemoselectivity

Air was employed as a green reoxidant of Pd(0), replacing stoichiometric and toxic silver salt, in the chelation-controlled Pd(II)-modulated arylative enolization of prop-2-en-1-ols to acquire synthetically-important β-aryl carbonyl derivatives. This green approach, which didn't require acid or base, allowed the compatibility of a range of functionalities (inclusive of -I, -Br & -Cl), resulting in the construction of structurally-diverse dihydrochalcones, α-benzyl-α′-alkyl acetones, α-benzyl β-keto esters and dihydrocinnamaldehydes. In addition to organoboronic acids, efficient coupling was also achieved with boronic esters and trifluoroborate salts. A deuterium labelling experiment revealed an interesting 1,2-hydrogen shift after β-arylation in the catalytic process. the Partner Organisations 2014.

Ligated regioselective PdII catalysis to access β-aryl-bearing aldehydes, ketones, and β-keto esters

By employing ligands in the PdII-mediated arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks β-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalities to generate dihydrochalcones, α-benzyl-α′- alkyl acetones, dihydrocinnamaldehydes, and α-benzyl β-keto esters (from Baylis-Hillman adducts). A practical multigram synthesis of an intermediate for Propafenone was also demonstrated. Copyright

Palladium(0) nanoparticle-catalyzed sp2 C-H activation: A convenient route to alkyl-aryl ketones by direct acylation of aryl bromides and iodides with aldehydes

Palladium(0) nanoparticles efficiently catalyze aliphatic aldehyde C-H functionalization by aryl halides to produce alkyl-aryl ketones in good yields. A wide range of substituted aryl and hetero-aryl bromides/iodides and open-chain aldehydes of varied chain length participated in this reaction.

Pd-catalyzed cross-coupling reactions of pyridine carboxylic acid chlorides with alkylzinc reagents

The efficient cross-coupling reaction to afford ketones from pyridine carboxylic acid chlorides and alkylzinc reagents in the presence of Pd(phen)Cl2 is reported. In the case of chloronicotinoyl chlorides, none of Negishi cross-coupling product