15441-04-0Relevant academic research and scientific papers
Nucleophilic and electrophilic double aroylation of chalcones with benzils promoted by the dimsyl anion as a route to all carbon tetrasubstituted olefins
Ragno, Daniele,Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Giovannini, Pier Paolo,Massi, Alessandro
, p. 1937 - 1945 (2015)
Dimsyl anion promoted the polarity reversal of benzils in a Stetter-like reaction with chalcones to give 2-benzoyl-1,4-diones (double aroylation products), which, in turn, were converted into the corresponding tetrasubstituted olefins via aerobic oxidative dehydrogenation catalyzed by Cu(OAc)2.
Cross-benzoin and Stetter-type reactions mediated by KO: T Bu-DMF via an electron-transfer process
Ragno, Daniele,Zaghi, Anna,Di Carmine, Graziano,Giovannini, Pier Paolo,Bortolini, Olga,Fogagnolo, Marco,Molinari, Alessandra,Venturini, Alessandro,Massi, Alessandro
, p. 9823 - 9835 (2016/10/31)
The condensation of aromatic α-diketones (benzils) with aromatic aldehydes (benzoin-type reaction) and chalcones (Stetter-type reaction) in DMF in the presence of catalytic (25 mol%) KOtBu is reported. Both types of umpolung processes proceed with good efficiency and complete chemoselectivity. On the basis of spectroscopic evidence (MS analysis) of plausible intermediates and literature reports, the occurrence of different ionic pathways have been evaluated to elucidate the mechanism of a model cross-benzoin-like reaction along with a radical route initiated by an electron-transfer process to benzil from the carbamoyl anion derived from DMF. This mechanistic investigation has culminated in a different proposal, supported by calculations and a trapping experiment, based on double electron-transfer to benzil with formation of the corresponding enediolate anion as the key reactive intermediate. A mechanistic comparison between the activation modes of benzils in KOtBu-DMF and KOtBu-DMSO systems is also described.
Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification
Zaghi, Anna,Ragno, Daniele,Di Carmine, Graziano,De Risi, Carmela,Bortolini, Olga,Giovannini, Pier Paolo,Fantin, Giancarlo,Massi, Alessandro
, p. 2719 - 2730 (2017/01/09)
A convenient heterogeneous continuous-flow procedure for the polarity reversal of aromatic α-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the two electron-tra
Synthesis of 1,4-diketones by Michael addition of O-aroylmandelonitriles involving rearrangement of aroyl group and decyanation
Miyashita,Matsuoka,Numata,Higashino
, p. 448 - 450 (2007/10/03)
The anions derived from O-aroylmandelonitriles 1 reacted with Michael addition acceptors such as acrylonitrile (7) and methyl acrylate (10) to give the corresponding 1,4-diketones 12, 13, and 15 in moderate to good yields. Under acidic conditions, the 1,4
