77669-94-4Relevant academic research and scientific papers
Selective α-Methylation of Aryl Ketones Using Quaternary Ammonium Salts as Solid Methylating Agents
Templ, Johanna,Schnürch, Michael
, p. 4305 - 4315 (2022/03/16)
We describe the use of phenyl trimethylammonium iodide (PhMe3NI) as an alternative methylating agent for introducing a CH3group in α-position to a carbonyl group. Compared to conventional methylating agents, quaternary ammonium salts have the advantages of being nonvolatile, noncancerogenic, and easy-to-handle solids. This regioselective method is characterized by ease of operational setup, use of anisole as green solvent, and yields up to 85%.
Enantioselective α-Arylation of Ketones via a Novel Cu(I)-Bis(phosphine) Dioxide Catalytic System
Escudero-Casao, Margarita,Licini, Giulia,Orlandi, Manuel
supporting information, p. 3289 - 3294 (2021/04/07)
A novel catalytic system based on copper(I) and chiral bis(phosphine) dioxides is described. This allows the arylation of silyl enol ethers to access enolizable α-arylated ketones in good yields and enantiomeric excess up to 95%. Noncyclic ketones are amenable substrates with this method, which complements other approaches based on palladium catalysis. Optimization of the ligand structure is accomplished via rational design driven by correlation analysis. Preliminary mechanistic hypotheses are also evaluated in order to identify the role of chiral bis(phosphine) dioxides.
Pd-catalyzed Fukuyama cross-coupling of secondary organozinc reagents for the direct synthesis of unsymmetrical ketones
Cherney, Alan H.,Reisman, Sarah E.
, p. 3259 - 3265 (2014/05/06)
The coupling of acyl electrophiles with organometallic reagents represents a convergent route toward complex and versatile ketone products. Despite the mild conditions and high functional group tolerance, the cross-coupling of carboxylic acid derivatives,
MECANISME DE L'ADDITION NUCLEOPHILE AU GROUPEMENT CARBONYLE-I. INFLUENCE DE LA NATURE DU SUBSTITUANT POLAIRE SUR LA STEREOCHIMIE ET LA REACTIVITE DANS LES REACTIONS D'ADDITION DE BROMURE DE METHYLMAGNESIUM AUX ARYL-1 PHENYL-2 PROPANONES
Lasperas, M.,Perez-Rubalcaba, A.,Quiroga-Feijoo, M. L.
, p. 3403 - 3408 (2007/10/02)
The influence of a m- or p-polar substituent in 1-aryl 2-phenyl propanones, on addition reactions with CH3MgBr in ether at 30 deg C has been investigated.The invariability of asymmetric induction as a function of substituent, and the correlation of rate constant ratios with Hammett ? constants (ρ=0.24, r=0.97), are consistent with a four-centre pericyclic concerted mechanism with concomitant departure of a solvent molecule.
