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Preparation of 1-Azido-2-Bromo-1,1,2,2-Tetrafluoroethane and Its Use in the Synthesis of N-Fluoroalkylated Nitrogen Heterocycles

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00532916" target="_blank" >RIV/61388963:_____/20:00532916 - isvavai.cz</a>

  • Alternative codes found

    RIV/00216208:11310/20:10414506

  • Result on the web

    <a href="https://doi.org/10.1021/acs.joc.0c01610" target="_blank" >https://doi.org/10.1021/acs.joc.0c01610</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acs.joc.0c01610" target="_blank" >10.1021/acs.joc.0c01610</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Preparation of 1-Azido-2-Bromo-1,1,2,2-Tetrafluoroethane and Its Use in the Synthesis of N-Fluoroalkylated Nitrogen Heterocycles

  • Original language description

    A straightforward synthesis of 1-azido-2-bromo-1,1,2,2-tetrafluoroethane on a multigram scale from 1,2-dibromotetrafluoroethane and sodium azide in a novel process initiated by organomagnesium compounds (i-PrMgCl·LiCl, turbo Grignard) is reported. Synthetic utility of the title azide in the preparation of N-tetrafluoroethylated and N-difluoromethylated five-membered nitrogen heterocycles was demonstrated with azide-alkyne cycloaddition to N-bromotetrafluoroethyl 1,2,3-triazoles, subsequent reduction to N-tetrafluoroethyl triazoles, rhodium-catalyzed transannulation with nitriles to N-tetrafluoroethylated imidazoles and rhodium-catalyzed ring-opening, and cyclization to N-difluoromethylated oxazoles and thiazoles.

  • 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

    10401 - Organic chemistry

Result continuities

  • Project

    <a href="/en/project/LTAUSA18037" target="_blank" >LTAUSA18037: Synthesis and reactivity of N-fluoroalkylated compounds</a><br>

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2020

  • 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

  • Volume of the periodical

    85

  • Issue of the periodical within the volume

    17

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    8

  • Pages from-to

    11482-11489

  • UT code for WoS article

    000569376800041

  • EID of the result in the Scopus database

    2-s2.0-85092211791