2077-40-9Relevant academic research and scientific papers
Combining photoredox-catalyzed trifluoromethylation and oxidation with dmso: Facile synthesis of α-trifluoromethylated ketones from aromatic alkenes
Tomita, Ren,Yasu, Yusuke,Koike, Takashi,Akita, Munetaka
supporting information, p. 7144 - 7148 (2014/07/21)
Trifluoromethylated ketones are useful building blocks for organic compounds with a trifluoromethyl group. A new and facile synthesis of ketones with a trifluoromethyl substituent in the α-position proceeds through a one-pot photoredox-catalyzed trifluoromethylation-oxidation sequence of aromatic alkenes. Dimethyl sulfoxide (DMSO) serves as a key and mild oxidant under these photocatalytic conditions. Furthermore, an iridium photocatalyst, fac[Ir(ppy)3] (ppy=2-phenylpyridine), turned out to be crucial for the present photoredox process. Valuable α-CF3-substituted ketones can be synthesized from aromatic alkenes by combining photoredox-catalyzed trifluoromethylation and oxidation with DMSO. The iridium photocatalyst fac-[Ir(ppy)3] (ppy=2-phenylpyridine) plays key roles in this keto-trifluoromethylation. SET=single electron transfer.
Wittig reaction: Role of steric effects in explaining the prevalent formation of Z olefin from nonstabilized ylides
Baccolini, Graziano,Delpivo, Camilla,Micheletti, Gabriele
, p. 1291 - 1302 (2012/11/13)
For understanding the mechanism involved in the Wittig reaction, it is important to know the factors which influence the stability of 1,2-oxaphosphetane intermediates with pentacoordinate phosphorus; in these intermediates, the steric factor plays a predominant role. Studying the Wittig reaction between nonstabilized ylides and different aldehydes, we noted that the stereochemical outcome driving toward Z-olefin formation was influenced only by different steric factors. The proposed mechanism differs from those previously reported because it underlines the fundamental role of the two cis/trans oxaphosphetane intermediates with the oxygen atom in equatorial position.
