Journal
HETEROCYCLES
Volume 77, Issue 2, Pages 1147-1161Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-08-S(F)94
Keywords
Benzimidazoline; Dimethoxypyrene; Photoinduced Electron Transfer; Radical Ion; Reductive Transformation
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Funding
- Uchida Energy Science Promotion Foundation
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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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