109398-10-9Relevant academic research and scientific papers
DMSO-Enabled Selective Radical O?H Activation of 1,3(4)-Diols
Han, Bing,Jiao, Ning,Jin, Rui,Liu, Guoquan,Liu, Jianzhong,Zhang, Ziyao,Zhu, Yuchao
supporting information, p. 19851 - 19856 (2020/09/04)
Control of selectivity is one of the central topics in organic chemistry. Although unprecedented alkoxyl-radical-induced transformations have drawn a lot of attention, compared to selective C?H activation, selective radical O?H activation remains less explored. Herein, we report a novel selective radical O?H activation strategy of diols by combining spatial effects with proton-coupled electron transfer (PCET). It was found that DMSO is an essential reagent that enables the regioselective transformation of diols. Mechanistic studies indicated the existence of the alkoxyl radical and the selective interaction between DMSO and hydroxyl groups. Moreover, the distal C?C cleavage was realized by this selective alkoxyl-radical-initiation protocol.
Organo cerium reagents in organic chemistry: General method of synthesis of alkyl substituted 1,3-diols by RLi-CeCl3 addition to β-hydroxyketones
Bartoli, Giuseppe,Bosco, Marcella,Van Beek, Jacco,Sambri, Letizia,Marcantoni, Enrico
, p. 2293 - 2296 (2007/10/03)
Organocerium compounds (RLi-CeCl3) are able to transfer an alkyl group to the carbonylic function of a β-hydroxyketone giving alkyl substituted 1,3-diols in excellent yields. The use of these not sophisticated reagents is essential to depress u
Nucleophilic Addition of Lanthanoid Metal Umpoled Diaryl Ketones to Electrophiles
Hou, Zhaomin,Takamine, Kan,Aoki, Osamu,Shiraishi, Hiroyuki,Fujiwara, Yuzo,Taniguchi, Hiroshi
, p. 6077 - 6084 (2007/10/02)
Ytterbium metal promoted cross-coupling reactions of diaryl ketones with a variety of electrophiles are described.Diaryl ketones treated with 1-2 equiv of Yb metal react smoothly with other ketones, nitriles, epoxides, CO2, etc., to give the corresponding unsymmetrical pinacols, α-hydroxy ketones, 1,3-diols, α-hydroxy carboxylic acids, etc., in good yields respectively.These reactions occur via nucleophilic addition of the intermediates 4a-c to electrophiles.Reaction of benzophenone (1a) with Yb metal is discussed in detail and some information on the composition of the intermediates of the reaction of diaryl ketones with Yb metal are also given.
