Facile Photochemical Transformation of Alkyl Aryl Selenides to the Corresponding Carbonyl Compounds by Molecular Oxygen: Use of Selenides as Masked Carbonyl Groups

被引:11
作者
Hyugano, Takeshi [1 ]
Liu, Suyou [2 ]
Ouchi, Akihiko [1 ,2 ]
机构
[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Ibaraki 3058571, Japan
[2] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
关键词
D O I
10.1021/jo801730j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkyl aryl selenides with and without functional groups on the alkyl group were transformed efficiently into the corresponding carbonyl compounds, particulary primary alkyl aryl selenides in good yields, by a simple photolysis in the presence of air or oxygen. This transformation can be conducted without protection of functional groups. The yield of carbonyl compounds was much affected by the solvent viscosity, reaction temperature, concentration of dissolved oxygen in the solvents, wavelength of light, and structure of the aryl substituents. The present study indicates that aryl selenides can be considered as a masked carbonyl group that can be easily converted to a carbonyl group by very mild reaction conditions even in the presence of various unprotected functional groups. Therefore, this functional group transformation can be used as an important tool in organic synthesis due to its simplicity and mild reaction condition.
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页码:8861 / 8866
页数:6
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