Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F23%3A43928096" target="_blank" >RIV/60461373:22340/23:43928096 - isvavai.cz</a>

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/10.1002/anie.202315162" target="_blank" >https://onlinelibrary.wiley.com/doi/10.1002/anie.202315162</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/anie.202315162" target="_blank" >10.1002/anie.202315162</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination

Popis výsledku v původním jazyce

N-Trifluoromethylated organics may be applied in drug design, agrochemical synthesis, and materials science, among other areas. Yet, despite recent advances in the synthesis of aliphatic, cyclic and heterocyclic N-trifluoromethyl compounds, no strategy based on trifluoromethyl nitrene has hitherto been explored. Here we describe the formation of triplet trifluoromethyl nitrene from azidotrifluoromethane, a stable and safe-to-use precursor, by visible light photocatalysis. The addition of CF3N to alkenes via biradical intermediates afforded previously unknown aziridines substituted with trifluoromethyl group on the nitrogen atom. The obtained aziridines were converted into either N-trifluoromethylimidazolines, via formal [3+2] cycloaddition with nitriles, mediated by a Lewis acid, or into N-trifluoromethylaldimines, via ring opening and aryl group migration mediated by a strong Brønsted acid. Our findings open new opportunities for the development of novel classes of N-CF3 compounds with possible applications in the life sciences. © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Název v anglickém jazyce

Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination

Popis výsledku anglicky

N-Trifluoromethylated organics may be applied in drug design, agrochemical synthesis, and materials science, among other areas. Yet, despite recent advances in the synthesis of aliphatic, cyclic and heterocyclic N-trifluoromethyl compounds, no strategy based on trifluoromethyl nitrene has hitherto been explored. Here we describe the formation of triplet trifluoromethyl nitrene from azidotrifluoromethane, a stable and safe-to-use precursor, by visible light photocatalysis. The addition of CF3N to alkenes via biradical intermediates afforded previously unknown aziridines substituted with trifluoromethyl group on the nitrogen atom. The obtained aziridines were converted into either N-trifluoromethylimidazolines, via formal [3+2] cycloaddition with nitriles, mediated by a Lewis acid, or into N-trifluoromethylaldimines, via ring opening and aryl group migration mediated by a strong Brønsted acid. Our findings open new opportunities for the development of novel classes of N-CF3 compounds with possible applications in the life sciences. © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GA23-07066S" target="_blank" >GA23-07066S: Časově závislé simulace pro časově rozlišené elektronové spektroskopie</a><br>

Návaznosti

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

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

ISSN

1433-7851

e-ISSN

1521-3773

Svazek periodika

63

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

"e202315162"

Kód UT WoS článku

001120087200001

EID výsledku v databázi Scopus

2-s2.0-85179357578