Synthesis of Azidodifluoromethyl Phenyl Sulfone and Its Use as a Synthetic Equivalent of the Azidodifluoromethyl Anion
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F23%3A00572194" target="_blank" >RIV/61388963:_____/23:00572194 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/23:10467045
Result on the web
<a href="https://doi.org/10.1021/acs.joc.3c00256" target="_blank" >https://doi.org/10.1021/acs.joc.3c00256</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.3c00256" target="_blank" >10.1021/acs.joc.3c00256</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of Azidodifluoromethyl Phenyl Sulfone and Its Use as a Synthetic Equivalent of the Azidodifluoromethyl Anion
Original language description
Azidodifluoromethyl phenyl sulfone, a new stable fluorinated azide, was synthesized on a multi-gram scale from difluoromethyl phenyl sulfone. The synthetic utility of the title azide in the preparation of N-difluoro(phenylsulfonyl)methyl-1,2,3-triazoles was demonstrated on examples of azide–alkyne cycloaddition reactions. Subsequent reductive desulfonylation/silylation afforded N-difluoro(trimethylsilyl)methyl-1,2,3-triazoles, and rhodium(II)-catalyzed transannulation with nitriles provided N-difluoro(phenylsulfonyl)methyl-substituted imidazoles. The title azide thus represents a synthetic equivalent of the azidodifluoromethyl anion.
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
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA23-04659S" target="_blank" >GA23-04659S: Utilization of organic fluorinated azides for the synthesis of unusual nitrogen heterocycles</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
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
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
88
Issue of the periodical within the volume
11
Country of publishing house
US - UNITED STATES
Number of pages
8
Pages from-to
6939-6946
UT code for WoS article
001010025800001
EID of the result in the Scopus database
2-s2.0-85161061260