Deazaalloxazines Flavin Derivatives That Provide Reductive Photoredox Catalysis with Inert Substrates

Result code in 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>

Alternative codes found

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

Result on the web

<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>

Result language

angličtina

Original language name

Deazaalloxazines Flavin Derivatives That Provide Reductive Photoredox Catalysis with Inert Substrates

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

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

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2025

Confidentiality

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

Name of the periodical

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

1521-3765

Volume of the periodical

31

Issue of the periodical within the volume

71

Country of publishing house

DE - GERMANY

Number of pages

11

Pages from-to

e02897

UT code for WoS article

001649668900037

EID of the result in the Scopus database

2-s2.0-105022637167