Flavin Photocatalysts for Visible-Light [2+2] Cycloadditions: Structure, Reactivity and Reaction Mechanism

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Publikace nespadá pod Filozofickou fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.
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MOJR Viktor PITROVA Gabriela STRAKOVA Karolina PRUKALA Dorota BRAZEVIC Sabina SVOBODOVA Eva HOSKOVCOVA Irena BURDZINSKI Gotard SLANINA Tomáš SIKORSKI Marek CIBULKA Radek

Rok publikování 2018
Druh Článek v odborném periodiku
Časopis / Zdroj CHEMCATCHEM
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
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Doi http://dx.doi.org/10.1002/cctc.201701490
Klíčová slova cycloaddition; energy transfer; natural products; photochemistry; reaction mechanisms
Popis 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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