Journal
CHEMCATCHEM
Volume 10, Issue 4, Pages 849-858Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201701490
Keywords
cycloaddition; energy transfer; natural products; photochemistry; reaction mechanisms
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Funding
- Ministry of Education, Youth and Sports of the Czech Republic [20-SVV/2017]
- Experientia Foundation
- Czech Science Foundation [16-09436S]
- programme Projects of Large Research, Development, and Innovations Infrastructures [LM2015042, LM2015085]
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New photocatalysts from the flavin family were found to mediate the [2+2] photocycloaddition reaction. 3-Butyl-10-methyl-5-deazaflavin (3a) and 1-butyl-7,8-dimethoxy-3-methylalloxazine (2e), if irradiated by visible light, were shown to allow an efficient (Phi approximate to 3-10%) intramolecular cyclisation of various types of substrates including substituted styrene dienes and bis(aryl enones), considered as electron-rich and electron-poor substrates, respectively, without any additional reagent. The versatility of the procedure was demonstrated by the cyclisation of photosensitive cinnamyl (E)-3-iodoallyl ether. Structure-activity studies found alloxazine 2e was more active than 7-monosubstituted (R = Cl, Br and MeO) alloxazines. The introduction of chlorine and bromine atom on the deazaflavin skeleton did not enhance the catalytic efficiency of 3a. A detailed electrochemical and spectroscopic study explains the reaction mechanism proceeding through energy transfer from the flavin excited triplet state to the diene followed by its cyclisation.
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