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Relative Electrophilic Fluorinating Power as Assayed by Competitive Catalytic Halogenation Reactions
Author(s) -
Toullec Patrick Y.,
Devillers Ingrid,
Frantz Richard,
Togni Antonio
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490240
Subject(s) - chemistry , selectfluor , halogenation , tetrafluoroborate , electrophile , electrophilic fluorination , catalysis , medicinal chemistry , acetonitrile , reagent , octane , organic chemistry , ionic liquid
Catalytic fluorination/chlorination competition experiments of β ‐keto ester 5 were used to assess the relative fluorinating activity of various electrophilic NF reagents (containing an NF bond). Thus, in the halogenation reactions catalyzed by the [Ti(TADDOLato)] complex 1 (=bis(acetonitrile)dichloro[(4 R ,5 R )‐2,2‐dimethyl‐ α , α , α ′, α ′‐tetra(naphthalen‐1‐yl)‐1,3‐dioxolane‐4,5‐dimethanolato(2−)‐ κO , κO ′]titanium), the activity range of a series of commercially available reagents spans more than two orders of magnitude. Selectfluor TM (=1‐(chloromethyl)‐4‐fluoro‐1,4‐diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate); 9 ; also called F‐TEDA; TEDA=triethylenediamine) reacts more than 100 times faster than 1‐fluoropyridinium tetrafluoroborate.