BENZIMIDAZOLINE-DIMETHOXYPYRENE. AN EFFECTIVE PROMOTER SYSTEM FOR PHOTOINDUCED ELECTRON TRANSFER PROMOTED REDUCTIVE TRANSFORMATIONS OF ORGANIC COMPOUNDS

被引:28
|
作者
Hasegawa, Eietsu [1 ]
Hirose, Harumi [1 ]
Sasaki, Kosuke [1 ]
Takizawa, Shinya [1 ]
Seida, Takayuki [1 ]
Chiba, Naoki [1 ]
机构
[1] Niigata Univ, Dept Chem, Fac Sci, Niigata 9502181, Japan
关键词
Benzimidazoline; Dimethoxypyrene; Photoinduced Electron Transfer; Radical Ion; Reductive Transformation; ALPHA; BETA-EPOXY KETONES; HYDROGEN-ATOM; CARBONYL-COMPOUNDS; HYDRIDE TRANSFER; ION-PAIRS; 1,3-DIMETHYL-2-PHENYLBENZIMIDAZOLINE; CYCLIZATION; OXIDATION; ACID;
D O I
10.3987/COM-08-S(F)94
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-(p-Methoxyphenyl)-1,3-dimethylbenzimidazoline (ADMBI) and 2-(o-hydroxyphenyl)-1,3-dimethylbenzimidazoline (HPDMBI) are used as reducing reagents in 1,8-dimethoxypyrene (1,8-DMP) sensitized, photoinduced electron transfer (PET) reactions. This system was effectively used for PET induced, reductive transformations of various organic substrates, including alpha,beta-epoxy ketones, the olefin tethered 2-bromomethyl-1-tetraone, and o-allyloxy-iodobenzene, as well as for the deprotection reactions of dodecyl-2-benzoylbenzoate and N-sulfonylindole. The results of studies show that 1,8-DMP is a more effective sensitizer than the previously used 9-methylcarbazole for deprotection of N-methyl-4-picolinium ester.
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页码:1147 / 1161
页数:15
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