74112-36-0Relevant articles and documents
Tropolonate salts as acyl-transfer catalysts under thermal and photochemical conditions: Reaction scope and mechanistic insights
Mai, Binh Khanh,Koenigs, Rene M.,Nguyen, Thanh Vinh,Lyons, Demelza J.M.,Empel, Claire,Pace, Domenic P.,Dinh, An H.
, p. 12596 - 12606 (2020/11/18)
Acyl-transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl-transfer reaction. Herein, we introduce a different acyl-transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give products under thermal or blue light photochemical conditions. Kinetic studies and density functional theory calculations suggest interesting mechanistic insights for reactions promoted by this acyl-transfer catalytic system.
CO2-expanded bio-based liquids as novel solvents for enantioselective biocatalysis
Hoang, Hai Nam,Nagashima, Yoshihiro,Mori, Shuichi,Kagechika, Hiroyuki,Matsuda, Tomoko
, p. 2984 - 2989 (2017/04/26)
For the first time, CO2-expanded bio-based liquids were reported as novel and sustainable solvents for biocatalysis. Herein, it was found that by expansion with CO2, 2-methyltetrahydrofuran (MeTHF), and other bio-based liquids, which were not favorable solvents for immobilized Candida antarctica lipase B (Novozym 435) catalyzed transesterification, were tuned into excellent reaction media. Especially, for the kinetic resolution of challenging bulky secondary substrates such as rac-1-adamantylethanol, the lipase displayed very high activity with excellent enantioselectivity (E value > 200) in CO2-expanded MeTHF (MeTHF concentration 10% v/v, 6 MPa), whereas there was almost no activity observed in conventional organic solvents.
Graphite oxide-catalyzed acetylation of alcohols and phenols
Liu, Yuan-Yuan,Qi, Jun-Mei,Bai, Li-Sha,Xu, Yue-Long,Ma, Ning,Sun, Fei-Fei
supporting information, p. 726 - 730 (2016/05/19)
Graphite oxide (GO) was used as a catalyst for the reactions of alcohols and phenols with acetic anhydride. The acetates of primary and secondary alcohols were prepared in good to excellent yields in short reaction time under mild conditions. Electron deficient phenols could be converted to the corresponding acetates steadily. As an efficient catalyst, GO is easily available, cheap, moderately toxic and weakly acidic.