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Electrophilic fluorination is the combination of a carbon-centered nucleophile with an electrophilic source of fluorine to afford organofluorine compounds. Although elemental fluorine and reagents incorporating an oxygen-fluorine bond can be used for this purpose, they have largely been replaced by reagents containing a nitrogen-fluorine bond. Some common fluorinating agents used for organic synthesis are N-fluoro-o-benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), and Selectfluor.

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  • Elektrofilní fluorace (cs)
  • Electrophilic fluorination (en)
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  • Elektrofilní fluorace je chemická reakce nukleofilu s uhlíkatým centrem a elektrofilního zdroje fluoru za vzniku organofluoridu. Pro tuto reakci lze použít elementární fluor i reaktanty obsahující vazby kyslík-fluor, ovšem nejčastěji se používají sloučeniny s vazbami dusík-fluor. K nejčastějším fluoračním činidlům v organické syntéze patří N-fluor-o-benzendisulfonimid (NFOBS), N-fluorbenzensulfonimid (NFSI) a selectfluor. (cs)
  • Electrophilic fluorination is the combination of a carbon-centered nucleophile with an electrophilic source of fluorine to afford organofluorine compounds. Although elemental fluorine and reagents incorporating an oxygen-fluorine bond can be used for this purpose, they have largely been replaced by reagents containing a nitrogen-fluorine bond. Some common fluorinating agents used for organic synthesis are N-fluoro-o-benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), and Selectfluor. (en)
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  • Elektrofilní fluorace je chemická reakce nukleofilu s uhlíkatým centrem a elektrofilního zdroje fluoru za vzniku organofluoridu. Pro tuto reakci lze použít elementární fluor i reaktanty obsahující vazby kyslík-fluor, ovšem nejčastěji se používají sloučeniny s vazbami dusík-fluor. Elektrofilní fluorace mohou být alternativou k nukleofilním fluoracím využívajícím fluoridy alkalických kovů nebo fluorid amonný či fluoridy síry. Vývoj reaktantů pro elektrofilní fluorace se převážně zaměřuje na snižování elektronové hustoty na atomu připojenému k fluoru; jako nejekonomičtější, nejstabilnější a nejbezpečnější reaktanty se ukázaly sloučeniny s vazbami dusík-fluor. Elektrofilní N-F reaktanty mohou být neutrální nebo kationtové a obsahovat sp2- i sp3-hybridizované dusíky. I když přesný mechanismus elektrofilní fluorace není znám, tak jsou popsány metody s vysokou účinností i stereoselektivitou. K nejčastějším fluoračním činidlům v organické syntéze patří N-fluor-o-benzendisulfonimid (NFOBS), N-fluorbenzensulfonimid (NFSI) a selectfluor. (cs)
  • Electrophilic fluorination is the combination of a carbon-centered nucleophile with an electrophilic source of fluorine to afford organofluorine compounds. Although elemental fluorine and reagents incorporating an oxygen-fluorine bond can be used for this purpose, they have largely been replaced by reagents containing a nitrogen-fluorine bond. Electrophilic fluorination offers an alternative to nucleophilic fluorination methods employing alkali or ammonium fluorides and methods employing sulfur fluorides for the preparation of organofluorine compounds. Development of electrophilic fluorination reagents has always focused on removing electron density from the atom attached to fluorine; however, compounds containing nitrogen-fluorine bonds have proven to be the most economical, stable, and safe electrophilic fluorinating agents. Electrophilic N-F reagents are either neutral or cationic and may possess either sp2- or sp3-hybridized nitrogen. Although the precise mechanism of electrophilic fluorination is currently unclear, highly efficient and stereoselective methods have been developed. Some common fluorinating agents used for organic synthesis are N-fluoro-o-benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), and Selectfluor. (en)
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