82745-72-0Relevant articles and documents
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
supporting information, p. 12724 - 12729 (2019/11/05)
An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
Ruthenium(II) oxidase catalysis for C-H alkenylations in biomass-derived γ-valerolactone
Bechtoldt, Alexander,Baumert, Marcel E.,Vaccaro, Luigi,Ackermann, Lutz
supporting information, p. 398 - 402 (2018/02/07)
Ruthenium(ii) biscarboxylate oxidase catalysis is a powerful tool for the assembly of functionalized arenes with oxygen as a green oxidant, but this strategy was thus far limited to its use in traditional organic solvents. Herein, we report on a green procedure for the ruthenium(ii) biscarboxylate-catalysed C-H functionalisation in biomass-derived γ-valerolactone as the reaction medium. The oxidase catalysis was characterized by ample substrate scope and proceeded efficiently with oxygen as the sole oxidant. The overall green nature of this C-H-activation methodology is reflected by H2O being the only by-product.