878652-50-7Relevant academic research and scientific papers
Visible-light-mediated oxidative dimerization of arylalkynes in the open air: Stereoselective synthesis of (Z)-1,4-enediones
Wei, Donglei,Liang, Fushun
supporting information, p. 5860 - 5863 (2016/11/29)
An organic photoredox catalytic one-pot protocol is developed for the highly stereoselective synthesis of (Z)-1,4-enediones. The reaction starts directly from alkyne precursors, using 4-(4-cyanophenyl)-2,6-diphenylpyrylium tetrafluoroborate (CN-TPT) as an efficient photosensitizer and dioxygen in the air as a green oxidant. A Csp-Csp oxidative coupling/[4 + 2] cyclization (with dioxygen)/fragmentive isomerization cascade mechanism was proposed. The predominant formation of (Z)-1,4-enediones is attributed to the efficient visible-light illumination from blue LEDs, along with possible energy transfer from the photosensitizer CN-TPT to the E-isomers.
ZnII- and AuI-catalyzed regioselective hydrative oxidations of 3-En-1-ynes with selectfluor: Realization of 1,4-dioxo and 1,4-oxohydroxy functionalizations
Jadhav, Appaso Mahadev,Gawade, Sagar Ashok,Vasu, Dhananjayan,Dateer, Ramesh B.,Liu, Rai-Shung
, p. 1813 - 1817 (2014/03/21)
Catalytic 1,4-dioxo functionalizations of 3-en-1-ynes to (Z)- and (E)-2-en-1,4-dicarbonyl compounds are described. This regioselective difunctionalization was achieved in one-pot operation through initial alkyne hydration followed by in situ Selectfluor oxidation. The presence of pyridine alters the reaction chemoselectivity to give 4-hydroxy-2-en-1-carbonyl products instead. A cooperative action of pyridine and ZnII assists the hydrolysis of key oxonium intermediate.
A highly tunable stereoselective dimerization of methyl ketone: Efficient synthesis of e - And Z-1,4-enediones
Xu, Kun,Fang, Yang,Yan, Zicong,Zha, Zhenggen,Wang, Zhiyong
supporting information, p. 2148 - 2151 (2013/06/05)
A new method for the tunable synthesis of 1,4-enedione directly from aromatic methyl ketone is described. This tandem reaction enables the construction of symmetric and unsymmetric 1,4-enediones with complete E-selectivity. Moreover, the resulting E-1,4-enedione could be transformed into a Z-isomer by irradiation with 23 W of white light.
