5333-22-2Relevant academic research and scientific papers
Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols
Huang, Fanping,Shao, Pan-Lin,Song, Jingyuan,Wang, Jiang,Zhang, Xumu
supporting information, p. 262 - 265 (2022/01/06)
Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herei
Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes
Zhang, Sheng,Bedi, Deepika,Cheng, Lu,Unruh, Daniel K.,Li, Guigen,Findlater, Michael
supporting information, p. 8910 - 8917 (2020/12/23)
Stereoselective synthesis of trisubstituted alkenes is a long-standing challenge in organic chemistry, due to the small energy differences between E and Z isomers of trisubstituted alkenes (compared with 1,2-disubstituted alkenes). Transition metal-catalyzed isomerization of 1,1-disubstituted alkenes can serve as an alternative approach to trisubstituted alkenes, but it remains underdeveloped owing to issues relating to reaction efficiency and stereoselectivity. Here we show that a novel cobalt catalyst can overcome these challenges to provide an efficient and stereoselective access to a broad range of trisubstituted alkenes. This protocol is compatible with both mono- and dienes and exhibits a good functional group tolerance and scalability. Moreover, it has proven to be a useful tool to construct organic luminophores and a deuterated trisubstituted alkene. A preliminary study of the mechanism suggests that a cobalt-hydride pathway is involved in the reaction. The high stereoselectivity of the reaction is attributed to both a π-πstacking effect and the steric hindrance between substrate and catalyst.
Electrooxidative formation of 1,2-diaroylcyclopropanes from 1,3-diaroylpropanes in the presence of KI
Okimoto, Mitsuhiro,Takahashi, Yukio,Kakuchi, Toyoji
, p. 207 - 208 (2007/10/03)
Various 1,2-diaroylcyclopropanes were obtained in good yields by the indirect electrochemical oxidation of 1,3-diaroylpropanes in the presence of catalytic amounts of KI under very mild conditions.
Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: Direct evidence for nucleophilic O-1,2-aryl shifts
Kamata, Masaki,Ohta, Motoko,Komatsu, Ken-Ichi,Kim, Hye-Sook,Wataya, Yusuke
, p. 2063 - 2067 (2007/10/03)
1,5-Diaryl-6,7-dioxabicyclo[3.2.2]nonanes 1a-d (1a: Ar=p-FC6H4, 1b: Ar=Ph, 1c: Ar=p-MeC6H4, 1d: Ar=p-MeOC6H4) were prepared by a modified method of photo-electron transfer oxygenation, and the reactions of 1 with FeBr2 were investigated under various conditions. The Fe(II)-induced degradation of 1 afforded various rearrangement products and fragmentation products through competitive single electron transfer (SET) and Lewis acid pathways. Direct evidence for the O-1,2-aryl shift was obtained by the isolation of rearrangement products, 1-aryloxy-5-aryl-8-oxabicyclo[3.2.1]octanes 8. The degradation mechanism was proposed and the in vitro antimalarial activities were also evaluated.
Novel photo-rearrangement of 1,5-di(p-methoxyphenyl)-6,7-dioxabicyclo[3.2.2]nonane through an O-neophyl-type 1,2-aryl shift: Evidence for a 1,6-dioxyl diradical intermediate
Kamata, Masaki,Komatsu, Ken-Ichi
, p. 9027 - 9030 (2007/10/03)
Photolysis and thermolysis of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonane 1a-c (a: Ar=p-MeOC6H4, b: Ar=p-MeC6H4, c: Ar=Ph) were investigated. (p-Methoxyphenyl)-substituted 1a underwent a novel photo-initiated O-neophyl-type 1,2-aryl shift to afford 1-(p-methoxyphenyl)oxy-5-(p-methoxyphenyl)-8-oxabicyclo[3.2.1]octane 7a along with a small amount of 1-(p-methoxyphenyl)-3-(2-(4′-methoxyphenyl)tetrahydrofuran-2-yl) propan-1-one 4a through an 1,6-dioxyl diradical intermediate, while the thermolysis mainly afforded the 1,5-di(p-methoxyphenyl)pentan-1,5-dione 5a and 1,4-di(p-methoxyphenyl)butan-1,4-dione 8a.
Photoinduced Electron Transfer (PET) cyclization and photooxygenation of 2,6-diaryl-1,6-heptadienes and 2,7-diaryl-1,7-octadienes
Griesbeck, Axel G.,Sadlek, Oliver,Polborn, Kurt
, p. 545 - 549 (2007/10/03)
The 2,6-diaryl-substituted 1,6-heptadienes 3a-c and the 2,7-diaryl-substituted 1,7-octadienes 4a-b were cleanly converted into the corresponding anellated cyclobutanes 5 and 6, resp., when irradiated under photoelectron-transfer conditions (9,10-dicyanoanthracene in acetonitrile). Only for 4c did the rearranged compound 7c become the dominant photoproduct. Oxygen trapping experiments with formation of endoperoxides 8, 9 were successful in the case of the electron-rich substrates 3b, c and 4c. VCH Verlagsgesellschaft mbH, 1996.
Highly Selective Aldol Reaction of Dibenzoylmethanes with Formaldehyde Catalyzed by Cobalt Schiff Base Complex under Neutral Conditions
Maruyama, Kazushige,Kubo, Katsunobu,Toda, Yukinobu,Kawase, Kazuhiko,Mashino, Takahiro,Nishinaga, Akira
, p. 5609 - 5612 (2007/10/02)
Coordinatively saturated hydroxocobalt(III) Schiff base complexes catalyze highly selective aldol reaction of dibenzoylmethanes with formaldehyde in methanol to give 1,3-dibenzoylpropanes, resulting from retro-Claisen reaction of 1,1,3,3-tetrabenzoylpropanes, which are obtained quantitatively in dichlorometane.Coordinatively saturated cobalt(III) Schiff base complexes ligating a substrate anion as a monodentate ligand is found to be the reactive species.
