330-68-7Relevant articles and documents
Site-Selective Tertiary Alkyl–Fluorine Bond Formation from α-Bromoamides Using a Copper/CsF Catalyst System
Nishikata, Takashi,Ishida, Syo,Fujimoto, Ryo
, p. 10008 - 10012 (2016)
A copper-catalyzed site-selective fluorination of α-bromoamides possessing multiple reaction sites, such as primary and secondary alkyl?Br bonds, using inexpensive CsF is reported. Tertiary alkyl?F bonds, which are very difficult to synthesize, can be formed by this fluorination reaction with the aid of an amide group. Control experiments revealed that in situ generated CuF2is a key fluorinating reagent that reacts with the tertiary alkyl radicals generated by the reaction between an α-bromocarbonyl compound and a copper(I) salt.
Substitution-reduction: An alternative process for the [ 18F]N-(2-fluoroethylation) of anilines
Briard, Emmanuelle,Pike, Victor W.
, p. 217 - 232 (2007/10/03)
Substitution of a halo atom (chloro or bromo) in easily prepared N-haloacetyl-anilines with no-carrier added (NCA) cyclotron-produced [ 18F]fluoride ion (18F, t1/2 = 109.8 min; β+ = 96.9%), followed by reduction with borane-tetrahydrofuran (BH3-THF), provides an alternative route to NCA [ 18F]N-(2-fluoroethyl)-anilines. This two-step and one-pot process is rapid (~50 min) and moderately high yielding (~40% decay-corrected radiochemical yield (RCY) overall). In the nucleophilic substitution reaction, 18-crown-6 is preferred to Kryptofix 222 as complexing agent for the solubilization of the counter-ion (K+), derived from an added metal salt, in acetonitrile. Weakly basic potassium bicarbonate is preferred as the added metal salt. Inclusion of a small amount of water, equating to 4-5 molar equivalents relative to 18-crown-6, base or precursor (held in equimolar ratio), is beneficial in preventing the adsorption of radioactivity onto the wall of the glass reaction vessel and for achieving high RCY in the nucleophilic substitution reaction. BH3-THF is effective for the rapid reduction of the generated [18F]N-fluoroacetyl-aniline to the [ 18F]N-(2-fluoroethyl)-aniline. Copyright
N-fluorosulfonimides and their application as fluorinating agents
-
, (2008/06/13)
The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.