59540-80-6

Upstream product

• 2046-18-6 4-phenylbutyronitrile 
• 300-57-2 allylbenzene 
• 123-72-8 butyraldehyde 
• 56293-04-0 1-phenyl-3-heptyne 
• 144741-88-8 1-phenylheptan-4-ol 
• 141-75-3 butyryl chloride 
• 2687-12-9 cinnamyl chloride 
• 6117-91-5 (E/Z)-2-buten-1-ol 
• 100-42-5 styrene 
• 1462-75-5 3-phenylpropylmagnesium bromide 
• 4119-41-9 1-iodo-3-phenylpropan 
• 106-94-5 propyl bromide 
• 18643-50-0 1-pentynyl lithium 
• 560095-63-8 (1-phenyl-3-hepten-4-yl)pentamethyl phosphoric triamide 

Relevant academic research and scientific papers

A General Approach to Intermolecular Olefin Hydroacylation through Light-Induced HAT Initiation: An Efficient Synthesis of Long-Chain Aliphatic Ketones and Functionalized Fatty Acids

Herein, an operationally simple, environmentally benign and effective method for intermolecular radical hydroacylation of unactivated substrates by employing photo-induced hydrogen atom transfer (HAT) initiation is described. The use of commercially available and inexpensive photoinitiators (Ph2CO and NHPI) makes the process attractive. The olefin hydroacylation protocol applies to a wide array of substrates bearing numerous functional groups and many complex structural units. The reaction proves to be scalable (up to 5 g). Different functionalized fatty acids, petrochemicals and naturally occurring alkanes can be synthesized with this protocol. A radical chain mechanism is implicated in the process.

Direct Access to Isotopically Labeled Aliphatic Ketones Mediated by Nickel(I) Activation

An extensive range of functionalized aliphatic ketones with good functional-group tolerance has been prepared by a NiI-promoted coupling of either primary or secondary alkyl iodides with NN2 pincer NiII-acyl complexes. The latter were easily accessed from the corresponding NiII-alkyl complexes with stoichiometric CO. This Ni-mediated carbonylative coupling is adaptable to late-stage carbon isotope labeling, as illustrated by the preparation of isotopically labelled pharmaceuticals. Preliminary investigations suggest the intermediacy of carbon-centered radicals.

SiO2-TBD as new heterogeneous catalyst for the nef conversion of secondary nitroalkanes under neat conditions

Treatment of secondary nitroalkanes with neat silica-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), at room temperature, allows the direct conversion of the secondary nitro groups to the corresponding keto carbonyls. Georg Thieme Verlag Stuttgart.

New ketone homoenolate anion equivalents derived from (alkenyl)pentamethyl phosphoric triamides

Lithiated ambident anions derived from (1-alkyl-2-propenyl)- or (1-phenyl-2-propenyl)-pentamethyl phosphoric triamides undergo regioselectively γ-reaction with various alkylating reagents and isobutyraldehyde. Further hydrolysis of adducts releases the ketone under acid conditions. Number of synthetic applications clearly show the ketone homoenolate behaviour of these new carbanions.

Synthesis of aliphatic ketones from allylic alcohols through consecutive isomerization and chelation-assisted hydroacylation by a rhodium catalyst

Abstract: An allylic alcohol, utilized as a precursor for an aliphatic aldehyde, reacted with olefins to afford aliphatic ketones in the presence of RhCl(PPh3)3, 2-amino-4-picoline, aniline, and benzoic acid through a tandem reaction of an isomerization and a chelation-assisted hydroacylation.

Unprecedented, selective Nef reaction of secondary nitroalkanes promoted by DBU under basic homogeneous conditions

Secondary nitrocompounds can be converted into the corresponding ketones under basic conditions using DBU in acetonitrile. Primary nitroalkanes are unaffected by these conditions. Elsevier Science Ltd. All rights reserved.

Rearrangement of (1,2,4-triazol-4-yl) ethanols to (1,2,4-triazol-1-yl)ethanols

The mechanism of rearrangement of β-hydroxyethyl-(1,2,4-triazoles) has been shown using crossover experiments to be intermolecular and free energy profiles show that reactions are thermodynamically-controlled.

Mercury in Organic Chemistry. 26. Synthesis of Heterocycles via Intramolecular Solvomercuration of Aryl Acetylenes

A number of ortho substituted aryl acetylenes, o-CH3XC6H4YCCR (X=O, S, CO2; Y=-, CO), have been observed to undergo facile intramolecular solvomercuration with mercuric acetate in acetic acid to afford the corresponding benzofuran, benzothiophene, isocoumarin, and chromone organomercuric chlorides, after aqueous sodium chloride workup.The aryl acetylenes m-XC6H4YCH2CCR (X=H, Y=O, R=CH3; X=CH3O, Y=CH2, R=n-C3H7) undergo similar cyclizations to yield mercurated 2H-1-benzopyrans and 1,2-dihydronaphthalenes.The mercuration and subsequent carbonylation of o-R1OC6H4CCR2 1=Si(t-Bu)Me2, R2=CH3; R1=CH3, R2=o-C6H4OCH3> has provided a new approach to the coumarin and coumestan ring systems.

Quaternary ammonium antiarrhythmic drugs

Quaternary ammonium salts of certain phenylbutylamines are useful antiarrhythmic drugs. A method for treating arrhythmia and prolonging the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such quaternary ammonium salts are disclosed.