Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination
Original language description
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.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
<a href="/en/project/GA23-07066S" target="_blank" >GA23-07066S: Time-dependent simulations for time-resolved electronic spectroscopies</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN
1433-7851
e-ISSN
1521-3773
Volume of the periodical
63
Issue of the periodical within the volume
2
Country of publishing house
DE - GERMANY
Number of pages
8
Pages from-to
"e202315162"
UT code for WoS article
001120087200001
EID of the result in the Scopus database
2-s2.0-85179357578