1766-85-4Relevant academic research and scientific papers
A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects
Ghinato, Simone,Territo, Davide,Maranzana, Andrea,Capriati, Vito,Blangetti, Marco,Prandi, Cristina
, p. 2868 - 2874 (2021/01/21)
We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.
Hydroacylation of 4-[18F]fluorobenzaldehyde: A novel method for the preparation of 4′-[18F]phenylketones
Khan, Noor-Ul Hasan,Lee, Byung Chul,Lee, Sang-Yoon,Choe, Yearn Seong,Jun, Chul-Ho,Chi, Dae Yoon
, p. 1045 - 1053 (2007/10/03)
To assess the potential of intermolecular hydroacylation reactions as a new fluorine-18 labeling method, model reactions of [18F]fluorobenzaldehyde with three different olefins (1-hexene (2a), allylbenzene (2b), and 3-phenoxypropene (2c)) in th
Direct conversion of benzyl alcohol to ketone by polymer-supported Rh catalyst
Jun, Chul-Ho,Hong, Hye-Suk,Huh, Chan-Woo
, p. 8897 - 8900 (2007/10/03)
Benzyl alcohol reacted with 1-alkene to give the corresponding ketone by in situ generated polystyrene-based rhodium catalyst. The catalytic activity of this polymer-supported rhodium catalyst has not been reduced after reusing it four times.
