208453-24-1Relevant articles and documents
Chemoselective reduction of aldehydes: Via a combination of NaBH4 and acetylacetone
Sui, Guoqing,Lv, Qingyun,Song, Xiaoqing,Guo, Huihui,Dai, Jiatong,Ren, Li,Lee, Chi-Sing,Zhou, Wenming,Hao, Hong-Dong
, p. 15793 - 15796 (2019/10/19)
A bench-stable combination of NaBH4-acetylacetone was developed for the efficient chemoselective reduction of aldehydes in the presence of ketones. This method offers a useful synthetic protocol for distinguishing carbonyl reaction sites, and its synthetic utility is reflected by its moisture tolerance and high efficiency in a variety of complex settings.
Cobalt(ii)-catalyzed benzylic oxidations with potassium persulfate in TFA/TFAA
Li, Tianlei,Li, Jishun,Zhu, Zihao,Pan, Weidong,Wu, Song
, p. 20879 - 20883 (2019/07/12)
A cobalt-catalyzed C(sp3)-H oxygenation reaction to furnish aldehyde was herein reported. This transformation demonstrated high chemo-selectivity, and tolerated various methylarenes bearing electron-withdrawing substituents. This reaction provided rapid access to diverse aldehydes form methylarenes. Notably, TFA/TFAA was used for the first time as a mixed solvent in cobalt-catalyzed oxygenation of benzylic methylenes.
Selective Aerobic Oxidation of Methylarenes to Benzaldehydes Catalyzed by N-Hydroxyphthalimide and Cobalt(II) Acetate in Hexafluoropropan-2-ol
Gaster, Eden,Kozuch, Sebastian,Pappo, Doron
supporting information, p. 5912 - 5915 (2017/05/12)
Efficient and highly selective catalytic conditions for the aerobic autoxidation of methylarenes to benzaldehydes, based on N-hydroxyphthalimide (NHPI) and cobalt(II) acetate in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), were developed. The sustainable conditions enable a multigram scale preparation of benzaldehyde derivatives in high efficiency and with excellent chemoselectivity (up to 99 % conversion and 98 % selectivity).
Development of a Rhodium(II)-Catalyzed Chemoselective C(sp3)-H Oxygenation
Lin, Yun,Zhu, Lei,Lan, Yu,Rao, Yu
supporting information, p. 14937 - 14942 (2015/10/19)
We report the first example of RhII-catalyzed chemoselective double C(sp3)-H oxygenation, which can directly transform various toluene derivatives into highly valuable aromatic aldehydes with great chemoselectivity and practicality. The critical combination of catalyst Rh(OAc)2, oxidant Selectfluor, and solvents of TFA/TFAA promises the successful delivery of the oxidation with satisfactory yields. A possible mechanism involving a unique carbene-Rh complex is proposed, and has been supported by both experiments and theoretical calculations.
Chemoselective synthesis of ketones and ketimines by addition of organometallic reagents to secondary amides
Bechara, William S.,Pelletier, Guillaume,Charette, Andre B.
experimental part, p. 228 - 234 (2012/06/01)
The development of efficient and selective transformations is crucial in synthetic chemistry as it opens new possibilities in the total synthesis of complex molecules. Applying such reactions to the synthesis of ketones is of great importance, as this motif serves as a synthetic handle for the elaboration of numerous organic functionalities. In this context, we report a general and chemoselective method based on an activation/addition sequence on secondary amides allowing the controlled isolation of structurally diverse ketones and ketimines. The generation of a highly electrophilic imidoyl triflate intermediate was found to be pivotal in the observed exceptional functional group tolerance, allowing the facile addition of readily available Grignard and diorganozinc reagents to amides, and avoiding commonly observed over-addition or reduction side reactions. The methodology has been applied to the formal synthesis of analogues of the antineoplastic agent Bexarotene and to the rapid and efficient synthesis of unsymmetrical diketones in a one-pot procedure. Macmillan Publishers Limited. All rights reserved.
A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents
Tokuyama, Hidetoshi,Yokoshima, Satoshi,Yamashita, Tohru,Fukuyama, Tohru
, p. 3189 - 3192 (2007/10/03)
A variety of ketones have been prepared by a palladium-catalyzed reaction of ethanethiol esters with organozinc reagents. Various functional groups, including esters, ketones, aromatic halides and aldehydes, tolerate the reaction conditions. The reaction can also be applied to the synthesis of α-amino ketones using the corresponding L-α-amino thiol esters without racemization.
