C-H amination reactions inside α-cyclodextrin supramolecular capsule
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F25%3A10506615" target="_blank" >RIV/00216208:11310/25:10506615 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11320/25:10506615
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=G2TtpGkQTE" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=G2TtpGkQTE</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d5ob01545f" target="_blank" >10.1039/d5ob01545f</a>
Alternative languages
Result language
angličtina
Original language name
C-H amination reactions inside α-cyclodextrin supramolecular capsule
Original language description
We describe the photochemical generation of an alkoxycarbonylnitrene species in a supramolecular capsule and its reactivity. 2-Adamantyl-carbonazidate was co-crystallized in a supramolecular capsule consisting of two alpha-cyclodextrins (α-CDs) interacting through a hydrogen bond network. Irradiation of the co-crystal with UV light (254 nm) in the solid state or in suspension resulted in the extrusion of a nitrogen molecule and the corresponding nitrene formation inside the capsule. This reactive species provides selective C-H amination of the capsule wall, specifically at carbon 5 of the α-CD unit. The supramolecular assembly fixes the geometry of both reactants, the nitrene and the C-H bond, in line, mimicking the transition state for the triplet nitrene H-atom-abstraction reaction. Enantioselective intramolecular formation of a minor product, a carbamate, occurring concomitantly in the CD capsule, helps clarify the mechanisms of C-H amination reactions.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic and Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
1477-0539
Volume of the periodical
23
Issue of the periodical within the volume
47
Country of publishing house
GB - UNITED KINGDOM
Number of pages
5
Pages from-to
10684-10688
UT code for WoS article
001619492000001
EID of the result in the Scopus database
2-s2.0-105022243639