- Visible-light-induced oxidative coupling of vinylarenes with diselenides leading to α-aryl and α-alkyl selenomethyl ketones
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A visible-light-induced oxidative coupling of diselenides with readily available vinylarenes is demonstrated. This benign protocol allows one to access a wide range of α-aryl and α-alkyl selenomethyl ketones in good yields with excellent functional group compatibility. The distinct advantages of this protocol over all previous methods include the use of a green solvent and air as an oxidant and the lack of a photocatalyst, a base, and an oxidant as well as better green chemistry matrices. Furthermore, the title reaction can be performed with natural sunlight, the most sustainable energy source imaginable. Additionally, the mild reaction conditions, easy operation and suitability for the modification of styrene-functionalized biomolecules make the current reaction system a more attractive method for the synthesis of a variety of medicinal and agrochemical compounds of interest.
- Liu, Gong-Qing,Yi, Wei,Wang, Peng-Fei,Liu, Ji,Ma, Meng,Hao, Da-Yun,Ming, Liang,Ling, Yong
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supporting information
p. 1840 - 1846
(2021/03/09)
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- Phenyl tributylstannyl selenide as a promising reagent for introducion of the phenylseleno group
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A new synthetic method of organoselenium compounds has been developed. When phenyl tributylstannyl selenide (PhSeSnBu3) was allowed to react with acyl or aroyl chlorides in the presence of a catalytic amount of a palladium complex such as Pd(PPh3)4, Se-phenyl selenol esters were obtained in moderate to good yields. Similarly, the palladium complex catalyzed the reaction of PhSeSnBu3 with α-halo carbonyl compounds to afford the corresponding α-phenyseleno carbonyl compounds in moderate yields.
- Nishiyama, Yutaka,Kawamatsu, Hiroaki,Funato, Saori,Tokunaga, Keiji,Sonoda, Noboru
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p. 3599 - 3602
(2007/10/03)
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- PHENYL SELENIUM TRICHLORIDE IN SYNTHESIS. REACTION WITH KETONES. A NEW VARIATION OF THE SELENOXIDE ELIMINATION REACTION
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Phenyl selenium trichloride was used for the introduction of a PhSeCl2-group into the α-position of ketones.These products were converted to enones (hydrolysis/selenoxide elimination) or α-phenylselenoketones (thiourea-reduction).
- Engman, Lars
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p. 6385 - 6388
(2007/10/02)
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