25062-46-8Relevant articles and documents
Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**
Murugesan, Kathiravan,Donabauer, Karsten,K?nig, Burkhard
supporting information, p. 2439 - 2445 (2020/12/07)
The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.
The local and natural sources in synthetic methods: the practical synthesis of aryl oximes from aryl aldehydes under catalyst-free conditions in mineral water
Goksu, H.,Orhan, E.
, (2021/07/27)
The synthesis of oximes from aryl aldehydes was prepared using hydroxylamine hydrochloride. The obtained oxime compounds were synthesized at maximum efficiency in mineral water at room temperature. The developed method is economical, practical and environmentally friendly. All of the aldehydes were converted the oxime a method using local sources and useful for industrial applications is introduced in the literature. Graphic abstract: In this study, addition elimination reaction, one of the important reactions of organic chemistry, was carried out using local sources. With this reaction, aryl oximes were obtained from aryl aldehydes in mineral water under catalyst-free conditions.[Figure not available: see fulltext.]
Visible-light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes
Chen, Hua,Deng, Hongmei,Gong, Haiying,Hao, Jian,Li, Mingjie,Peng, Yi,Wan, Wen,Wang, Qian,Zhang, Yifang
supporting information, p. 7867 - 7874 (2021/09/28)
A visible light mediated stereospecific C(sp2)-H difluoroalkylation of (Z)-aldoximes to (E)-difluoroalkylated ketoximes has been described. In this reaction, (hetero)-aromatic and aliphatic difluoroalkylated ketoximes could be obtained with the retention of the configuration of the starting aldoximes. A preliminary mechanism study showed that a difluoromethyl radicalviaan SET pathway was involved.
