Deazaalloxazines Flavin Derivatives That Provide Reductive Photoredox Catalysis with Inert Substrates

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F25%3A00644397" target="_blank" >RIV/61388955:_____/25:00644397 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/25:43933364 RIV/60461373:22810/25:43933364

Výsledek na webu

<a href="https://hdl.handle.net/11104/0374254" target="_blank" >https://hdl.handle.net/11104/0374254</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.202502897" target="_blank" >10.1002/chem.202502897</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Deazaalloxazines Flavin Derivatives That Provide Reductive Photoredox Catalysis with Inert Substrates

Popis výsledku v původním jazyce

Reductive transformations of substances that are difficult to reduce continue to pose challenges for photoredox catalysis. Promising photoreduction catalysts include flavin and deazaflavin derivatives, however, even their reductive abilities are limited for the range of substrates considered ´inert´. In this work, we present 5-deazaalloxazines, a new group of deazaflavin analogues that are predisposed to catalyze reductions due to their low reduction potential (down to1.65 V vs. SCE) even in the ground state. We studied three series of 5-deazaalloxazines ([i] 5-unsubstituted, [ii] 5-aryldeazaalloxazines, and [iii] 5-trifluoromethyl-5-deazaalloxazines) to determine their photophysical and electrochemical properties and their ability to participate in model photoreduction reactions. From 31 compounds, we selected 1,3-dimethyl-7,8-dimethoxy-5-(o-tolyl)-5-deazaalloxazine [3a(o-MePh)], as it showed, among other things, the highest efficiency in photodehalogenation of p-fluoroanisole and was photostable and absorbed in the visible light region, thereby allowing photoreactions using a 400 nm LED. Practical applicability was demonstrated in the C-P coupling reaction of electron-rich aryl halides (including chloroanisoles and p-fluoroanisole) with trimethyl phosphite, providing an arylation reaction to form dimethyl arylphosphonates, and in the release/deprotection of amines from the corresponding tosyl and triflylamides.

Název v anglickém jazyce

Deazaalloxazines Flavin Derivatives That Provide Reductive Photoredox Catalysis with Inert Substrates

Popis výsledku anglicky

Reductive transformations of substances that are difficult to reduce continue to pose challenges for photoredox catalysis. Promising photoreduction catalysts include flavin and deazaflavin derivatives, however, even their reductive abilities are limited for the range of substrates considered ´inert´. In this work, we present 5-deazaalloxazines, a new group of deazaflavin analogues that are predisposed to catalyze reductions due to their low reduction potential (down to1.65 V vs. SCE) even in the ground state. We studied three series of 5-deazaalloxazines ([i] 5-unsubstituted, [ii] 5-aryldeazaalloxazines, and [iii] 5-trifluoromethyl-5-deazaalloxazines) to determine their photophysical and electrochemical properties and their ability to participate in model photoreduction reactions. From 31 compounds, we selected 1,3-dimethyl-7,8-dimethoxy-5-(o-tolyl)-5-deazaalloxazine [3a(o-MePh)], as it showed, among other things, the highest efficiency in photodehalogenation of p-fluoroanisole and was photostable and absorbed in the visible light region, thereby allowing photoreactions using a 400 nm LED. Practical applicability was demonstrated in the C-P coupling reaction of electron-rich aryl halides (including chloroanisoles and p-fluoroanisole) with trimethyl phosphite, providing an arylation reaction to form dimethyl arylphosphonates, and in the release/deprotection of amines from the corresponding tosyl and triflylamides.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10405 - Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

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

Název periodika

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

1521-3765

Svazek periodika

31

Číslo periodika v rámci svazku

71

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

11

Strana od-do

e02897

Kód UT WoS článku

001649668900037

EID výsledku v databázi Scopus

2-s2.0-105022637167