73252-30-9Relevant articles and documents
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.
Chemoselective oxidation by electronically tuned nitroxyl radical catalysts
Hamada, Shohei,Furuta, Takumi,Wada, Yoshiyuki,Kawabata, Takeo
supporting information, p. 8093 - 8097 (2013/08/23)
Electronic tuning: Nitroxyl radical 1 is shown to be an efficient catalyst for the oxidation of secondary alcohols, and promotes oxidation through an oxoammonium species which is highly reactive because of the adjacent electron-withdrawing ester groups. Chemoselective oxidation of benzylic alcohols in the presence of aliphatic alcohols is observed and is proposed to proceed by a rate-determining hydride transfer. Copyright
Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3
Parvanak Boroujeni, Kaveh
experimental part, p. 621 - 630 (2010/11/04)
Aromatic compounds react smoothly with carboxylic acids in the presence of silica gel supported aluminium trichloride to afford the corresponding ketones with high regioselectivity in high to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency. tuebitak.