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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F18%3A00111730" target="_blank" >RIV/00216224:14310/18:00111730 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/18:43917088

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/full/10.1002/cctc.201701490" target="_blank" >https://onlinelibrary.wiley.com/doi/full/10.1002/cctc.201701490</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cctc.201701490" target="_blank" >10.1002/cctc.201701490</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/LM2015085" target="_blank" >LM2015085: CERIT Scientific Cloud</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

CHEMCATCHEM

ISSN

1867-3880

e-ISSN

1867-3899

Svazek periodika

10

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

10

Strana od-do

849-858

Kód UT WoS článku

000425626700026

EID výsledku v databázi Scopus

2-s2.0-85040707825