General approach to 2-fluoroalkyl 1,3-azoles via the tandem ring opening and defluorinative annulation of N-fluoroalkyl-1,2,3-triazoles
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00509347" target="_blank" >RIV/61388963:_____/19:00509347 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/19:10401462
Result on the web
<a href="https://pubs.rsc.org/en/content/articlelanding/2019/QO/C9QO01104H#!divAbstract" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2019/QO/C9QO01104H#!divAbstract</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c9qo01104h" target="_blank" >10.1039/c9qo01104h</a>
Alternative languages
Result language
angličtina
Original language name
General approach to 2-fluoroalkyl 1,3-azoles via the tandem ring opening and defluorinative annulation of N-fluoroalkyl-1,2,3-triazoles
Original language description
Rhodium-catalyzed transformation of N-fluoroalkyl-1,2,3-triazoles in the presence of tert-butyl carbamate or water provided an efficient route to 2-fluoroalkyl imidazoles and 2-fluoroalkyl oxazoles, respectively. The treatment of N-fluoroalkyl-1,2,3-triazoles with excess water gave fluoroalkylated ketamides which were cyclized in situ to 2-fluoroalkyl oxazoles or thiazoles. Trifluoromethyl- and other difluoroalkyl-substituted heterocycles were obtained by the present method. The mechanism of this cascade transformation involving carbene insertion, HF elimination and cyclization was proposed.
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
<a href="/en/project/LTAUSA18037" target="_blank" >LTAUSA18037: Synthesis and reactivity of N-fluoroalkylated compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic Chemistry Frontiers
ISSN
2052-4129
e-ISSN
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Volume of the periodical
6
Issue of the periodical within the volume
22
Country of publishing house
GB - UNITED KINGDOM
Number of pages
5
Pages from-to
3776-3780
UT code for WoS article
000494737700009
EID of the result in the Scopus database
2-s2.0-85074666798